INTERNATIONAL UNION OF PURE
AND APPLIED CHEMISTRY
and
INTERNATIONAL UNION OF BIOCHEMISTRY
AND MOLECULAR BIOLOGY
JOINT COMMISSION ON BIOCHEMICAL NOMENCLATURE~
NOMENCLATURE OF CARBOHYDRATES
(Recommendations 1996)
Prepared Jot publication by
ALAN D. McNAUGHT
The Royal Society of Chemistry, Thomas Graham House, Science Park, Milton
Road, Cambridge CB4 4WF, UK
*Members of the Commission (JCBN) at various times during the work on this document (1983-1996) were as
follows:
Chairmen: H.B.F. Dixon (UK), J.F.G. Vliegenthart (Netherlands), A. Cornish-Bowden (France); Secretaries: A. Comish-Bowden (France), M.A. Chester (Sweden), A.J. Barrett (UK), J.C. Rigg (Netherlands);
Members: J.R. Bull (RSA), R. Cammack (UK), D. Coucouvanis (USA), D. Horton (USA), M.A.C.
Kaplan (Brazil), P. Karlson (Germany), C. Li6becq (Belgium), K.L. Loening (USA), G.P. Moss (UK),
J. Reedijk (Netherlands), K.F. Tipton (Ireland), S. Velick (USA), P. Venetianer (Hungary).
Additional contributors to the formulation of these recommendations:
Expert Panel: D. Horton (USA) (Convener), O. Achmatowicz (Poland), L. Anderson (USA), S.J. Angyal
(Australia), R. Gigg (UK), B. Lindberg (Sweden), D.J. Manners (UK), H. Paulsen (Germany), R. Schauer
(Germany).
Nomenclature Committee oflUBMB (NC-IUBMB) (those additional to JCBN): A. Bairoch (Switzerland),
H. Berman (USA), H. Bielka (Germany), C.R Cantor (USA), W. Saenger (Germany), N. Sharon (israel),
E. van Lenten (USA), E.C. Webb (Australia).
American Chemical Society Committee jor Carbohydrate Nomenclature: D. Horton (Chairman), L.
Anderson, D.C. Baker, H.H. Baer, J.N. BeMiller, B. Bossenbroek, R. W. Jeanloz, K.L. Loening, W. A.
Szarek, R.S. Tipson, W.J. Whelan, R.L. Whistler.
Corresponding Members of the ACS Committee,lbr Carbohydrate Nomenclature (other than JCBN and
the expert panel): R.F. Brady (USA), J.S. Brimacombe (UK), J.G. Buchanan (UK), B. Coxon (USA), J.
Defaye (France), N.K. Kochetkov (Russia), R.U. Lemieux (Canada), R.H. Marchessault (Canada), J.M.
Webber (UK).
Correspondence oil these recommendations should be addressed to Dr. Alan D. McNaught at the above
address or to any member of the Commission.
Reproduced fromPureAMd. Chem.. 1996.68, 1919. Copyright © 1996 InternationalUnionof Pure and Applied Chemistry
{IUPAC). Publishedby ElsevierScience Ltd.
NOMENCLATURE OF CARBOHYDRATES
(Recommendations 1996)
Contents
Preamble
2-Carb-O. Historical development of carbohydrate nomenclature
0. l.
0.2.
0.3.
0.4.
Early approaches
The contribution of Emil Fischer
Cyclic forms
Nomenclature commissions
2-Carb-1. Definitions and conventions
1,1. Carbohydrates
1.2. Monosaccharides (aldoses and ketoses)
1.3. Dialdoses
1.4. Diketoses
1.5. Ketoaldoses (aldoketoses)
1.6. Deoxy sugars
1.7. Amino sugars
1.8. Alditols
1.9. Aldonic acids
1.10. Ketoaldonic acids
1.11. Uronic acids
1.12. Aldaric acids
1.13. Glycosides
1.14. Oligosaccharides
1.15. Polysaccharides
1.16. Conventions for examples
2-Carb-2, Parent monosaccharides
2.1. Choice of parent structure
2.2. Numbering and naming of the parent structure
2-Carb-3. The Fischer projection of the acyclic form
2-Carb-4. Configurational symbols and prefixes
4.1.
4,2.
4.3.
4.4.
4.5.
Use of D and L
The configurational atom
Configurational prefixes in systematic names
Racemates and meso forms
Optical rotation
2-Carb-5. Cyclic forms and their representation
5.1.
5.2.
5.3.
5.4.
5.5.
5.6.
5.7.
5.8.
Ring size
The Fischer projection
Modified Fischer projection
The Haworth representation
Unconventional Haworth representations
The Mills depiction
Depiction of conformation
Conformations of acyclic chains
2-Carb-6. Anomeric forms; use of o~and
6.1.
6.2.
6.3.
6.4.
The anomeric centre
The anomeric reference atom and the anomeric configurational symbol
Mixtures of anomers
Use of o~and 13
2-Carb-7. Conformation of cyclic forms
7.1.
7.2.
7,3.
7.4.
The conformational descriptor
Notation of ring shape
Notation of variants
Enantiomers
2-Carb-8. Aldoses
8.1. Trivial names
8.2. Systematic names
8.3. Multiple configurational prefixes
8.4. Multiple sets of chiral centres
8.5. Anomeric configuration in cyclic forms of higher aldoses
2-Carb-9. Dialdoses
2-Carb- l O. Ketoses
10.1. Classification
10.2. Trivial names
10.3. Systematic names
10.4. Configurational prefixes
2-Carb-11. Diketoses
11.1. Systematic names
11.2. Multiple sets of chiral centres
2-Carb-12. Ketoaldoses (aldoketoses, aldosuloses)
12.1. Systematic names
12.2. Dehydro names
2-Carb-13. Deoxy sugars
13.1. Trivial names
13.2. Names derived from trivial names of sugars
13.3. Systematic names
13.4. Deoxy alditols
2-Carb-14. Amino sugars
14. I. General principles
14.2. Trivial names
14.3. Systematic names
2-Carb-15. Thio sugars and other chalcogen analogues
2-Carb-16. Other substituted monosaccharides
16.1. Replacement of hydrogen at a non-terminal carbon atom
16.2. Replacement of OH at a non-terminal carbon atom
16.3. Unequal substitution at a non-terminal carbon atom
16.4. Terminal substitution
16.5. Replacement of carbonyl oxygen by nitrogen (imines, hydrazones, osazones etc.)
16.6. Isotopic substitution and isotopic labelling
2-Carb-17. Unsaturated monosaccharides
17.1. General principles
17.2. Double bonds
17.3. Triple bonds and cumulative double bonds
2-Carb-18. Branched-chain sugars
18.1. Trivial names
18.2. Systematic names
18.3. Choice of parent
18.4. Naming the branches
18.5. Numbering
18.6. Terminal substitution
2-Carb-19. Alditols
19.1. Naming
19.2. meso Forms
2-Carb-20. Aldonic acids
20.1. Naming
20.2. Derivatives
2-Carb-21. Ketoaldonic acids
21.1. Naming
21.3. Derivatives
2-Carb-22. Uronic acids
22.1. Naming and numbering
22.2. Derivatives
2-Carb-23. Aldaric acids
23.1. Naming
23.2. meso Forms
23.3. Trivial names
23.4. Derivatives
2-Carb-24. O-Substitution
24. I. Acyl (alkyl) names
24.2. Phosphorus esters
24.3. Sulfates
2-Carb-25. N-Substitution
2-Carb-26. Intramolecular anhydrides
2-Carb-27. Intermolecular anhydrides
2-Carb-28. Cyclic acetals
2-Carb-29. Hemiacetals and hemithioacetals
2-Carb-30. Acetals, ketals and their thio analogues
2-Carb-3 I. Names for monosaccharide residues
31.1. Glycosyi residues
31.2. Monosaccharides as substituent groups
31.3. Bivalent and tervalent residues
2-Carb-32. Radicals, cations and anions
2-Carb-33. Glycosides and glycosyl compounds
33.1. Definitions
33.2. Glycosides
33.3. Thioglycosides.
33.4. Selenoglycosides
33.5. Glycosyl halides
33.6. N-Glycosyl compounds (glycosylamines)
33.7. C-Glycosyl compounds
2-Carb-34. Replacement of ring oxygen by other elements
34.1. Replacement by nitrogen or phosphorus
34.2. Replacement by carbon
2-Carb-35. Carbohydrates containing additional rings
35.1. Use of bivalent substituent prefixes
35.2. Ring fusion methods
35.3. Spiro systems
2-Carb-36. Disaccharides
36.1. Definition
36.2. Disaccharides without a free hemiacetal group
36.3. Disaccharides with a free hemiacetal group
36.4. Trivial names
2-Carb-37. Oligosaccharides
37.1. Oligosaccharides without a free hemiacetal group
37.2. Oligosaccharides with a free hemiacetal group
37.3. Branched oligosaccharides
37.4. Cyclic oligosaccharides
37.5. Oligosaccharide analogues
2-Carb-38. Use of symbols for defining oligosaccharide structures
38.1. General considerations
38.2. Representations of sugar chains
38.3. The extended form
38.4. The condensed form
38.5. The short form
2-Carb-39. Polysaccharides
39.1. Names for homopolysaccharides
39.2. Designation of configuration of residues
39.3. Designation of linkage
39.4. Naming of newly discovered polysaccharides
39.5. Uronic acid derivatives.
39.6. Amino sugar derivatives
39.7. Polysaccharides composed of more than one kind of residue
39.8. Substituted residues
39.9. Glycoproteins, proteoglycans and peptidoglycans
References
Appendix
Trivial Names for Carbohydrates, with their Systematic Equivalents
Glossary of Glycose-based Terms
Preamble
These Recommendations expand and replace the Tentative Rules for Carbohydrate Nomenclature [ 1] issued
in 1969 jointly by the IUPAC Commission on the Nomenclature of Organic Chemistry and the IUB-IUPAC
Commission on Biochemical Nomenclature (CBN) and reprinted in [2]. They also replace other published
JCBN Recommendations [3-7] that deal with specialized areas of carbohydrate terminology; however, these
documents can be consulted for further examples. Of relevance to the field, though not incorporated into the
present document, are the following recommendations:
Nomenclature of cyclitols, 1973 [8]
Numbering of atoms in myo-inositol, 1988 [9]
Symbols for specifying the conformation of polysaccharide chains, 1981 [10]
Nomenclature of glycoproteins, glycopeptides and peptidoglycans, 1985 [ 11 [
Nomenclature of glycolipids, in preparation [ 12]
The present Recommendations deal with the acyclic and cyclic forms of monosaccharides and their simple
derivatives, as well as with the nomenclature of oligosaccharides and polysaccharides. They are additional to
the Definitive Rules for the Nomenclature of Organic Chemistry [13,14] and are intended to govern those
aspects of the nomenclature of carbohydrates not covered by those rules.
2-Carb-O. Historical development of carbohydrate nomenclature [15]
2-Carb-0.1. Early approaches
In the early nineteenth century, individual sugars were often named after their source, e.g. grape sugar
(Traubenzucker) for glucose, cane sugar (Rohrzucker) for saccharose (the name sucrose was coined much
later). The name glucose was coined in 1838; Kekul6 in 1866 proposed the name 'dextrose' because glucose
is dextrorotatory, and the laevorotatory 'fruit sugar' (Fruchtzucker, fructose) was for some time named
'laevulose' (American spelling 'levulose'). Very early, consensus was reached that sugars should be named
with the ending '-ose', and by combination with the French word 'cellule' for cell the term cellulose was
coined, long before the structure was known. The term 'carbohydrate' (French 'hydrate de carbone') was
applied originally to monosaccharides, in recognition of the fact that their empirical composition can be
expressed as Cn(H20)n. However the term is now used generically in a wider sense (see 2-Carb-1.1).
2-Carb-0.2. The contribution of Emil Fischer
Emil Fischer [ 16] began his fundamental studies on carbohydrates in 1880. Within ten years, he could assign
the relative configurations of most known sugars and had also synthesized many sugars. This led to the
necessity to name the various compounds. Fischer and others laid the foundations of a terminology still in
use, based on the terms triose, tetrose, pentose, and hexose. He endorsed Armstrong's proposal to classify
sugars into aldoses and ketoses, and proposed the name fructose for laevulose, because he found that the sign
of optical rotation was not a suitable criterion for grouping sugars into families.
The concept of stereochemistry, developed since 1874 by van't Hoff and Le Bel, had a great impact on
carbohydrate chemistry because it could easily explain isomerism. Emil Fischer introduced the classical
projection formulae for sugars, with a standard orientation (carbon chain vertical, carbonyl group at the top);
since he used models with flexible bonds between the atom s , he could easily 'stretch' his sugar models into
a position suitable for projection. He assigned to the dextrorotatory glucose (via the derived glucaric acid)
the projection with the OH group at C-5 pointing to the right, well knowing that there was a 50% chance that
this was wrong. Much later (Bijvoet, 1951), it was proved correct in the absolute sense.
Rosanoff in 1906 selected the enantiomeric glyceraldehydes as the point of reference; any sugar derivable by
chain lengthening from what is now known as D-glyceraldehyde belongs to the D series, a convention still in
use.
2-Carb-0.3. Cyclic forms
Towards the end of the nineteenth century it was realized that the free sugars (not only the glycosides) existed
as cyclic hemiacetals or hemiketals. Mutarotation, discovered in 1846 by Dubrunfaut, was now interpreted
as being due to a change in the configuration of the glycosidic (anomeric) carbon atom. Emil Fischer assumed
the cyclic form to be a five-membered ring, which Tollens designated by the symbol <1,4>, while the
six-membered ring received the symbol < 1,5>.
In the 1920s, Haworth and his school proposed the terms 'furanose' and 'pyranose' for the two forms. Haworth
also introduced the 'Haworth depiction' for writing structural formulae, a convention that was soon widely
followed.
2-Carb-0.4. Nomenclature commissions
Up to the 1940s, nomenclature proposals were made by individuals; in some cases they were followed by the
scientific community and in some cases not. Official bodies like the International Union of Chemistry, though
developing and expanding the Geneva nomenclature for organic compounds, made little progress with
carbohydrate nomenclature. The IUPAC Commission on Nomenclature of Biological Chemistry put forward
a classification scheme for carbohydrates, but the new terms proposed have not survived. However in 1939
the American Chemical Society (ACS) formed a committee to look into this matter, since rapid progress in
the field had led to various misnomers arising from the lack of guidelines. Within this committee, the
foundations of modem systematic nomenclature for carbohydrates and derivatives were laid: numbering of
the sugar chain, the use of D and L and o~ and 13, and the designation of stereochemistry by italicized prefixes
(multiple prefixes for longer chains). Some preliminary communications appeared, and the final report,
prepared by M.L. Wolfrom, was approved by the ACS Council and published in 1948 [17].
Not all problems were solved, however, and different usages were encountered on the two sides of the Atlantic.
A joint British-American committee was therefore set up, and in 1952 it published 'Rules for Carbohydrate
Nomenclature' [18]. This work was continued, and a revised version was endorsed in 1963 by the American
Chemical Society and by the Chemical Society in Britain and published [19]. The publication of this report
led the IUPAC Commission on Nomenclature of Organic Chemistry to consider the preparation of a set of
IUPAC Rules for Carbohydrate Nomenclature. This was done jointly with the IUPAC-IUB Commission on
Biochemical Nomenclature, and resulted in the 'Tentative Rules for Carbohydrate Nomenclature, Part I,
1969', published in 1971/72 in several joumals [1]. It is a revision of this 1971 document that is presented
here. In the present document, recommendations are designated 2-Carb-n, to distinguish them from the Carb-n
recommendations in the previous publication.
2-Carb-1. Definitions and conventions
2-Carb-l.1. Carbohydrates
The generic term 'carbohydrate' includes monosaccharides, oligosaccharides and polysaccharides as well as
substances derived from monosaccharides by reduction of the carbonyl group (alditols), by oxidation of one
or more terminal groups to carboxylic acids, or by replacement of one or more hydroxy group(s) by a hydrogen
atom, an amino group, a thiol group or similar heteroatomic groups. It also includes derivatives of these
compounds. The term 'sugar' is frequently applied to monosaccharides and lower oligosaccharides. It is
noteworthy that about 3% of the compounds listed by Chemical Abstracts Service (i.e. more than 360 000)
are named by the methods of carbohydrate nomenclature.
Note. Cyclitols are generally not regarded as carbohydrates. Their nomenclature is dealt with in other recommendations
[8,9].
2-Carb-l.2. Monosaceharides
Parent monosaccharides are polyhydroxy aldehydes H-[CHOH]n-CHO or polyhydroxy ketones H-[CHOH]nCO-[CHOH]m-H with three or more carbon atoms.
The generic term 'monosaccharide' (as opposed to oligosaccharide or polysaccharide) denotes a single unit,
without glycosidic connection to other such units. It includes aldoses, dialdoses, aldoketoses, ketoses and
diketoses, as well as deoxy sugars and amino sugars, and their derivatives, provided that the parent compound
has a (potential) carbonyl group.
1.2.1. Aldoses and ketoses
Monosaccharides with an aldehydic carbonyl or potential aldehydic carbonyl group are called aldoses; those
with a ketonic carbonyl or potential ketonic carbonyl group, ketoses.
Note. The term 'potential aldehydic carbonyl group' refers to the hemiacetal group arising from ring closure. Likewise,
the term 'potential ketonic carbonyl group' refers to the hemiketat structure (see 2-Carb-5).
1.2.2. Cyclic forms
Cyclic hemiacetals or hemiketals of sugars with a five-membered (tetrahydrofuran) ring are called furanoses,
those with a six-membered (tetrahydropyran) ring pyranoses. For sugars with other ring sizes see 2-Carb-5.
2-Carb-l.3. Diaidoses
Monosaccharides containing two (potential) aldehydic carbonyl groups are called dialdoses (see 2-Carb-9).
2-Carb-l.4. Diketoses
Monosaccharides containing two (potential) ketonic carbonyl groups are termed diketoses (see 2-Carb-1 I).
2-Carb-l.5. Ketoaldoses (aldoketoses, aldosuloses)
Monosaccharides containing a (potential) aldehydic group and a (potential) ketonic group are called ketoaldoses (see 2-Carb-12); this term is preferred to the alternatives on the basis of 2-Carb-2.1.1 (aldose preferred
to ketose).
2-Carb-l.6. Deoxy sugars
Monosaccharides in which an alcoholic hydroxy group has been replaced by a hydrogen atom are called deoxy
sugars (see 2-Carb- 13).
2-Carb-l.7 Amino sugars
Monosaccharides in which an alcoholic hydroxy group has been replaced by an amino group are called amino
sugars (see 2-Carb-14). When the hemiacetal hydroxy group is replaced, the compounds are called glycosylamines.
2-Carb-l.8. Alditols
The polyhydric alcohols arising formally from the replacement of a carbonyl group in a monosaccharide with
a CHOH group are termed alditols (see 2-Carb-19).
2-Carb-l.9. Aldonic acids
Monocarboxylic acids formally derived from aldoses by replacement of the aldehydic group by a carboxy
group are termed aldonic acids (see 2-Carb-20).
2-Carb-l.10. Ketoaldonic acids
Oxo carboxylic acids formally derived from aldonic acids by replacement of a secondary CHOH group by a
carbonyl group are called ketoaldonic acids (see 2-Carb-21).
2 - C a r b - l . l l . Uronic acids
Monocarboxylic acids formally derived from aldoses by replacement of the CH2OH group with a carboxy
group are termed uronic acids (see 2-Carb-22).
2-Carb-l.12. Aldaric acids
The dicarboxylic acids formed from aldoses by replacement of both terminal groups (CHO and CH2OH) by
carboxy groups are called aldaric acids (see 2-Carb-23).
2-Carb-l.13. Glycosides
Glycosides are mixed acetals formally arising by elimination of water between the hemiacetal or hemiketal
hydroxy group of a sugar and a hydroxy group of a second compound. The bond between the two components
is called a glycosidic bond.
For an extension of this definition, see 2-Carb-33.
2-Carb-l.14. Oligosaeeharides
Oligosaccharides are compounds in which monosaccharide units are joined by glycosidic linkages. According
to the number of units, they are called disaccharides, trisaccharides, tetrasaccharides, pentasaccharides etc.
The borderline with polysaccharides cannot be drawn strictly; however the term 'oligosaccharide' is
commonly used to refer to a defined structure as opposed to a polymer of unspecified length or a homologous
mixture. When the linkages are of other types, the compounds are regarded as oligosaccharide analogues.
(See 2-Carb-37.)
10
Note. This definition is broader than that given in [6], to reflect current usage.
2-Carb-l.15. Polysaccharides
'Polysaccharide' (glycan) is the name given to a macromolecule consisting of a large number of monosaccharide (glycose) residues joined to each other by glycosidic linkages. The term poly(glycose) is not a full
synonym for polysaccharide (glycan) (cf. [20]), because it includes macromolecules composed of glycose
residues joined to each other by non-glycosidic linkages.
For polysaccharides containing a substantial proportion of amino sugar residues, the term polysaccharide is
adequate, although the term glycosaminoglycan may be used where particular emphasis is desired.
Polysaccharides composed of only one kind of monosaccharide are described as homopolysaccharides
(homoglycans). Similarly, if two or more different kinds of monomeric unit are present, the class name
heteropolysaccharide (heteroglycan) may be used. (See 2-Carb-39.)
The term 'glycan' has also been used for the saccharide component of a glycoprotein, even though the chain
length may not be large.
The term polysaccharide has also been widely used for macromolecules containing glycose or alditol residues
in which both glycosidic and phosphate diester linkages are present.
2-Carb-l.16. Conventions for examples
1.16.1. Names of examples are given with an initial capital letter (e.g. 'L-glycero-~-D-gluco-Heptopyranose')
to clarify the usage in headings and to show which letter controls the ordering in an alphabetical index.
1.16.2. The following abbreviations are commonly used for substituent groups in structural formulae: Ac
(acetyl), Bn or PhCH2 (benzyl), Bz or PhCO (benzoyl), Et (ethyl), Me (methyl), Me3Si (not TMS)
(trimethylsilyl), ButMe2Si (not TBDMS) (tert-butyldimethylsilyl), Ph (phenyl), Tf (triflyl = trifluoromethanesulfonyl), Ts (tosyl = toluene-p-sulfonyl), Tr (trityl).
2-Carb-2. Parent monosaccharides
2-Carb-2.1. Choice of p a r e n t structure
In cases where more than one monosaccharide structure is embedded in a larger molecule, a parent structure
is chosen on the basis of the following criteria, applied in the order given until a decision is reached:
2.1.1. The parent that includes the functional group most preferred by general principles of organic
nomenclature [ 13,14]. If there is a choice, it is made on the basis of the greatest number of occurrences of the
most preferred functional group. Thus aldaric acid > uronic acid/ketoaldonic acid/aldonic acid > dialdose >
ketoaldose/aldose > diketose > ketose.
2.1.2. The parent with the greatest number of carbon atoms in the chain, e.g. a heptose rather than a hexose.
2.1.3. The parent with the name that comes first in an alphabetical listing based on:
2.1.3.1. the trivial name or the configurational prefix(es) of the systematic name, e.g. allose rather than
glucose, a gluco rather than a gulo derivative;
2.1.3.2. the configurational symbol
D
rather than L ;
2.1.3.3. the anomeric symbol cc rather than 13.
2.1.4. The parent with the most substituents cited as prefixes (bridging substitution, e.g. 2,3-O-methylene, is
regarded as multiple substitution for this purpose).
2.1.5. The parent with the lowest locants (see [ 14], p. 17) for substituent prefixes.
2.1.6. The parent with the lowest locant for the first-cited substituent.
The implications of these recommendations for branched-chain structures are exemplified in 2-Carb-18.
Note 1. To maintain homomorphic relationships between classes of sugars, the (potential) aldehyde group of a uronic
acid is regarded as the principal function for numbering and naming (see 2-Carb-2.2.1 and 2-Carb-22).
Note 2. To maintain integrity of carbohydrate names, it is sometimes helpful to overstep the strict order of principal
group preference specified in general organic nomenclature [ 13,14]. For example, a carboxymethyl-substituted sugar
can be named as such, rather than as an acetic acid derivative (see 2-Carb-31.2).
II
2-Carb-2.2. Numbering and naming the parent structure
The basis for the name is the structure of the parent monosaccharide in the acyclic form. Charts I and IV
(2-Carb-10) give trivial names for parent aldoses and ketoses with up to six carbon atoms. 2-Carb-8.2 and
2-Carb-10.3 describe systematic naming procedures.
CHO
H--(~--OH
CH2OH
D-Glyceraldehyde
D-glycero
CHO
CHO
H--C--OH
H--C--OH
HO--C--H
H--C--OH
(~H2OH
D-Erythrose
CH2OH
O-Threose
D.threo
D-erythro
CHO
CHO
H--C--OH
H--C--OH
H--C--OH
CHO
H--C--OH
HO-C--H
H--C--OH
HO--C--H
HO-C--H
H--C--OH
CH2OH
D-Ribose
(~H2OH
D-Arabinose
(~H2OH
D-Xylose
(~H2OH
D-Lyxose
D-ribo
D-arabino
i
(D-Rib)
CHO
H--C~OH
'
H--I~OH
H--C--OH
H--(~--OH
(~H2OH
D-Allose
D-a#o
CHO
HO--C--H
H--C--OH
H--C--OH
CHO
CHO
HO--6 --H
H-- (5--OH
H--(~--OH HO--C--H
i
H--C--OH
H--C--OH
H--C--OH
H--C--OH
(~H2OH
(~H2OH
D-Altrose D-Glucose
(D-All)
D-xylo
(D-Ara)
D-altro
(D-AIt)
D-gluco
(D-GIc)
CHO
Ho--C--H
.
HO--(~--H
.
CHO
H--C~OH
.
H--C--OH
H--C--OH
H--,C--OH
HO--C,~ H
H--C--OH
CH2OH
o-Mannose
(~H2OH
D-Gulose
D-manno
(D-Man)
D-lyxo
(O-Xyl)
D-gulo
(D-Gul)
(D-Lyx)
CHO
HO-C--H
.
.
H--C--OR
CHO
H--C--OH
HO--C--H
HO--C,--H
HO--C--H
H--C--OH
H--C--OH
(~H2OH
D-Idose
D-ido
(D-Ido)
(~HzOH
D-Galactose
D-galacto
(D-Gal)
CHO
HO-C--H
HO-C--H
i
HO-C--H
H-C--OH
(~H2OH
D-Talose
D-talo
(D-Tal)
Chart I. Trivial names (with recommended three-letter abbreviations in parentheses) and structures (in the
aldehydic, acyclic form) of the aldoses with three to six carbon atoms. Only the D-forms are shown; the
L-forms are the mirror images. The chains of chiral atoms delineated in bold face correspond to the
configurational prefixes given in italics below the names
2.2.1. Numbering
The carbon atoms of a monosaccharide are numbered consecutively in such a way that:
2.2.1.1. A (potential) aldehyde group receives the locant 1 (even if a senior function is present, as in uronic
acids; see 2-Carb-2.1, note 1);
2.2.1.2. The most senior of other functional groups expressed in the suffix receives the lowest possible locant,
i.e. carboxylic acid (derivatives) > (potential) ketonic carbonyl groups.
2.2.2. Choice of parent name
The name selected is that which comes first in the alphabet (configurational prefixes included). Trivial names
are preferred for parent monosaccharides and for those derivatives where all stereocentres are stereochemically
unmodified.
12
Examples:
CH2OH
HOCH
HCOH
CH2OH
I
HOCH
HOCH
I
HCOH
I
HOCH
HOCH
HOCH
I
L-erythro
-
I
CH2OH
L-Glucitol
not D-gulitoI
-
HOCH
HOCH
I
L-gluco
C----O
CH2OH
L-erythro-L-gluco-Non-5-ulose
not D-threo-D-allo-non-5-ulose
2.2.3. Choice between alternative names for substituted derivatives
When the parent structure is symmetrical, preference between alternative names for derivatives should be
given according to the following criteria, taken in order:
2.2.3.1. The name including the configurational symbol D rather than L.
Example:
CH2OH
I
HCOH
I
HOCH
I
HCOMe
I
CH2OH
4-O-MethyI-D-xylitol
not 2- O-methyl-L-xylitol
2.2.3.2. The name that gives the lowest set of ]ocants (see [14], p. 17) to the substituents present.
Example:
ICH2OH
MeOCH
I
MeOCH
1
HCOH
I
HCOMe
t
CH2OH
2,3,5-Tri-O-methyI-D-mannitol
not 2,4,5-tri-O-methyI-D-mannitol
2.2.3.3. The name that, when the substituents have been placed in alphabetical order, possesses the lowest
locant for the first-cited substituent.
Example:
OH
CIH2
AcOCH
I
HOCH
I
HCOH
I
HCOMe
I
CH2OH
2- O-Acetyl-5-O-methyl-D-mannitol
not 5-O-acetyl-2-O-methyI-D-mannitol
2-Carb-3. The F i s c h e r
projection of the acyclicform
In this representation of a monosaccharide, the carbon chain is written vertically, with the lowest numbered
carbon atom at the top. To define the stereochemistry, each carbon atom is considered in turn and placed in
the plane of the paper. Neighbouring carbon atoms are below, and the H and OH groups above the plane of
the paper (see below).
13
H
OH
~-
(a)
HPC-OH
~-
(b)
H--C-OH
-=
H--C--OH
~
HCOH
I
[
I
(c)
(d)
(e)
~-
H
OH
=-
(f)
OH
(g)
Conventional representation of a carbon atom (e.g. C-2 of D-glucose) in the Fischer projection.
Representation (e) will be used in general in the present document.
The formula below is the Fischer projection for the acyclic form of D-glucose. The Fischer projections of the
other aldoses (in the acyclic form) are given in Chart I (2-Carb-2.2).
1OHO
21
HCOH
31
HOCH
41
HCOH
sI
HCOH
61
CH2OH
D-Glucose
Note. The Fischer projection is not intended to be a true representation of conformation.
2-Carb-4. Configurational symbols and pre~es
2-Carb-4.1. Use of D and L
The simplest aldose is glyceraldehyde (occasionally called glyceral [21]). It contains one centre of chirality
(asymmetric carbon atom) and occurs therefore in two enantiomeric forms, called D-glyceraldehyde and
L-glyceraldehyde; these are represented by the projection formulae given below. It is known that these
projections correspond to the absolute configurations. The configurational symbols D and L should appear in
print in small-capital roman letters (indicated in typescript by double underlining) and are linked by a hyphen
to the name of the sugar.
CHO
...
...CHO
H--(~--OH
HO--C--H
CH2OH
CH2OH
D-Glyceraldehyde
L-Glyceraldehyde
2-Carb-4.2. The configurational atom
A monosaccharide is assigned to the D or the L series according to the configuration at the highest-numbered
centre of chirality. This asymmetrically substituted carbon atom is called the 'configurational atom'. Thus if
the hydroxy group (or the oxygen bridge of the ring form; see 2-Carb-6) projects to the right in the Fischer
projection, the sugar belongs to the D series and receives the prefix D-.
Examples:
CHO
I
?HO
HCOH
I
HOCH
I
HCOH
I
HCOH
I
CH2OH
CHO
I
HCOH
I
HOCH
t
HCOH
I
CH2OH
CH20H
C=O
I
HOCH
I
HCOH
I
HCOH
I
CH2OH
D-Glucose
D-Xylose
D-arabino-Hex-2-ulose
(D-Fructose)
D Monosaccharides
HOCH,
HOCH
I
HCOH
1
HOCH
I
HCOH
I
CH2OH
D-glycero-L-gulo-Heptose
14
CHO
I
HOCH
I
HCOH
HOCH
HOCH
HOCH
I
HCOH
I
HOCH
L
CH2OH
I
CH2OH
L-Arabinose
L-Glucose
HOCH
HOCH
I
I
C=O
I
HCOH
HOCH
CHO
I
HOCH
[
CHO
I
CHzOH
CH2OH
L-xy/o-Hex-2-ulose
(L-Sorbose)
I
I
HCOH
HCOH
I
HOCH
I
CH2OH
L-glycero-D-manno-Heptose
L Monosaccharides
2-Carb-4.3. Configurational prefixes in systematic names
In the systematic names of sugars or their derivatives, it is necessary to specify not only the configuration of
the configurational atom but also the configurations of all CHOH groups. This is done by the appropriate
configurational prefix. These prefixes are derived from the trivial names of the aldoses in Chart I (relevant
portions of the structures are delineated in bold face). In monosaccharides with more than four asymmetrically
substituted carbon atoms, where more than one configurational prefix is employed (see 2-Carb-8.3), each
group of asymmetrically substituted atoms represented by a particular prefix has its own configurational
symbol, specifying the configuration (D or L) of the highest numbered atom of the group.
The configurational prefixes are printed in lower-case italic (indicated in typescript by underlining), and are
preceded by either 13- or L-, as appropriate. For examples see 2-Carb-4.2 and 2-Carb-6.2
Note. In cyclic forms of sugars, the configuration at the anomeric chiral centre is defined in relation to the 'anomeric
reference atom' (see 2-Carb-6.2).
2-Carb-4.4.
Racemates and meso forms
Racemates may be indicated by the prefix DE-. Structures that have a plane of symmetry and are therefore
optically inactive (e.g. erythritol, galactitol) are called meso forms and may be given the prefix 'meso-'.
2-Carb-4.5.
Optical rotation
If the sign of the optical rotation under specified conditions is to be indicated, this is done by adding (+)- or
(-)- before the configurational prefix. Racemic forms are indicated by (_+)-.
Examples:
D-Glucose or (+)-D-glucose
D-Fructose or (-)-D-fructose
DE-Glucose or (+)-glucose
2-Carb-5. Cyclic forms and their representation
2-Carb-5.1. Ring size
Most monosaccharides exist as cyclic hemiacetals or hemiketals. Cyclic forms with a three-membered ring
are called oxiroses, those with a four-membered ring oxetoses, those with a five-membered ring furanoses,
with a six-membered ring pyranoses, with a seven-membered ring septanoses, with an eight-membered ring
octanoses, and so on. To avoid ambiguities, the locants of the positions of ring closure may be given; the
locant of the carbonyl group is always cited first, that of the hydroxy group second (for relevant examples of
this see 2-Carb-6.4). Lack of ring size specification has no particular implication.
Note. The 'o' of oxirose, oxetose, and octanose is not elided after a prefix ending in 'o'.
Example:
Nonooctanose, not nonoctanose.
If it is to be stressed that an open-chain form of an aldose is under consideration, the prefix 'aldehydo-' may
be used. For ketoses, the prefix is 'keto-'
2-Carb-5.2. The Fischer projection
If a cyclic form of a sugar is to be represented in the Fischer projection, a long bond can be drawn between
the oxygen involved in ring formation and the (anomeric) carbon atom to which it is linked, as shown in the
following formulae for cyclic forms of ¢X-D-glucose (see 2-Carb-6 for the meaning of ~ and 13):
1 f
H~O---~
I
HOCH
.#o./
/HCOH
H?OH /
l
HCOH
I
HCOH
I
CH2OH
~-D-Glucooxirose
'
HCOH
I
HCOH
I
CH2OH
HOCH
HCOH
HCO----"
I
HCOH
I
~
I
HCO ~
H?OH
HO?H
H?OH
H?OH
l
I
CH2OH
~-D-Glucooxetose
1
H?OH [
HOCH|
"-----OCH
CH2OH
~-D-Glucofuranose ~-D-Glucopyranose
CH20
~-D-Glucoseptanose
2-Carb-5.3. Modified Fischer projection
To clarify steric relationships in cyclic forms, a modified Fischer projection may be used. The carbon atom
bearing the ring-forming hydroxy group, C-n (C-5 for glucopyranose) is rotated about its bond to C-(n - 1)
(C-4 for glucopyranose) in order to bring all ring atoms (including the oxygen) into the same vertical line.
The oxygen bridge is then represented by a long bond; it is imagined as being behind the plane of the paper.
Examples are given below.
l
HCOH
I
HCOH
I
HOCH
I
HCOH
HCOH
I
HCOAc
I
AcOCH OAc
I
..-"
HC--C--H
I
HOCH2--?H
?
~-D-Glucopyranose
HCOH
I
HOCH
I
HCOH
I
HCOH
1
_ _ ~ )I
\
I
H~-cH3
I
HOCH2--CHI
oJ
?
13-L-Fucopyranose
~-D-Fructofuranose
CH2OAc
2,3,5,6-Tetra-O-acetylc~-D-galactofuranose
/
HOC--CH2OH
I
HOCH
I
HCOH
Thus the trans relationship between the hydroxymethyl group and the C- 1 hydroxy group in O~-D-glucopyranose, and the cis relationship between the methyl group and the C- 1 hydroxy group in 13-L-fucopyranose, are
clearly shown. Note that representation of ketoses may require a different modification of the Fischer
projection, as shown in the fructofuranose example above. Here C-2 is rotated about the bond with C-3 to
accommodate the long bond to C-2 from the oxygen at C-5.
2-Carb-5.4 The Haworth representation
This is a perspective drawing of a simplified model. The ring is orientated almost perpendicular to the plane
of the paper, but viewed from slightly above so that the edge closer to the viewer is drawn below the more
distant edge, with the oxygen behind and C-1 at the right-hand end. To define the perspective, the ring bonds
closer to the viewer are often thickened.
The following schematic representation of pyranose ring closure in D-glucose shows the reorientation at C-5
necessary to allow ring formation; this process corresponds to the change from Fischer to modified Fischer
projection.
ICHO
(,,.
iH...,x,
HCOH
~I/(~H
I
HOCH
'
HCOH
I
HCOH
I
6CH2OH
6 CH20 H
J" 6
~,
H
oH
H
H
OH
CHO
,
H
R, oH
6 CH20 H
Ok\
H/C--H
H H
H, OH
H
H
H
OH
H
OH
Haworth representation of D-glucopyranose
The orientation of the model described above results in a clockwise numbering of the ring atoms. Groups that
appear to the right of the modified Fischer projection appear below the plane of the ring; those on the left
16
appear above. In the common Haworth representation of the pyranose form of D-aldohexoses, C-6 is above
the plane.
Generally, the configuration at the centre that yields the ring oxygen determines whether the rest of the carbon
chain is below or above the plane of the ring.
Examples (for the use of c~and 13see 2-Carb-6):
i.~o" I ~'
•
.foil
H.OO. _----
H OH
2o.
~ '
Fischer
y ~ o ~
y
__= . OH
1
.co. /
modified
Fischer
Haworth
CH20--"
OH
13-L-Arabinofuranose representations
OH
I~-D-Ribopyranose
OPO32I
HO
OH
13-D-Ribofuranose5-phosphate
~O 1
HOCH2-- H
HO,~H
/
--
HCOH I
HCOH/
CH20-j
H
H/'~
H
OPO32I
ON,CHzOH
HO/¢~
HOC~
OH
OH H
~HI "?-,~
H ~
OH
HO H
CC-D-Fructopyranose
et-D-Fructofuranose 1,6-bisphosphate
.oc.
.?o.
,coH
|
/
/
-
~H20~
.C3.
.o
T
oH
H
Methyl C~-D-glucoseptanoside
HI~ ~'~tOMe
.o~.y.
HOCHI OH
CH2OH
Methyl c~-L-altrooxetoside
?H2OH
HOCH
z
HOCH
HOCH
~OMe
H
H
Methyl 13-o-allooxiroside
Note. In writing Haworth formulae, the H atoms bound to the carbon atoms of the ring are often omitted to avoid
crowding of the lettering in the ring. For the sake of clarity, the form with H atoms included is preferred in this document.
2-Carb-5.5. Unconventional H a w o r t h representations
It is sometimes desirable to draw Haworth formulae with the ring in other orientations (see Chart II), when
there are bulky substituents to be represented, or when linkages in oligo- or poly-saccharides are to be shown.
If the ring is inverted [as in (g)-(1)], the numbering runs counterclockwise.
17
CH2OH
H/~s
H
~HH
H
H
\ OH
1
H~
O
.°
CH2OH
~
OH
OH
OH
OH
(a)
H
H
~
HO ~1
H
H
of H
(c)
(b)
H
H
0
H
H
OH
H
OH
1[
HOCH20
o ~ O H
H" O
~1.~ ~ H
5~ OH
H
H
(d)
OH
OH
\H
OH
H
H
H
CH2OH
(h)
H
H
OH
H O ~
1
(g)
OH
H
H
H
(f)
(e)
H
HO ~
OH
H
CH2OH
0)
OH
H
.H//O
~OH
1~/
HOCH2~
o
H
HOCH2~ -
[1
OH
OH
0)
H
H
OH
(I)
(k)
Chart II. I~-D-Glucopyranose in the twelve possible Haworth representations
(the hydrogen atoms are frequently omitted)
2-Carb-5.6. The Mills depiction
In some cases, particularly where additional rings are present, structural formulae can be clarified by use of
the Mills depiction. Here the main hemiacetal ring is drawn in the plane of the paper; dashed bonds denote
substituents below this plane, and thickened bonds those above.
O'k/~__~..~OH
Examples:
CH2OH
o
.fH
O,.._~- O~,,,,,O
Me2J__ O~-~"-.b./~CMe2
1,2:3,4-D -O- sopropyl,dene-~-D-galactopyranose
D-Glucaro-1,4:6,3-dilaetone
2-Carb-5.7. Depiction ot" conformation
The Haworth representation implies a planar ring. However, monosaccharides assume conformations that are
not planar: these may be represented by Haworth conformational formulae. The nomenclature of conformations is described in 2-Carb-7. For example, ~-D-glucopyranose assumes a chair conformation:
I
H
CH2OH ~'
CH2OH ~
\
HO~~@OH
H
HO-,~...."'~"~..&~
OH
OH
H
iS-D-Glucopyranosein a chair conformation
18
Note. The hydrogen atoms bonded to carbon are frequently omitted, but their inclusion may be necessary to make a
stereochemical point.
2-Carb-5.8. Conformations of acyclic chains
Conformational depictions of acyclic sugar chains are conveniently expressed by locating certain atoms in
the plane of the paper and orientating the remaining atoms or groups appropriately above and below that
plane, as shown for D-arabinitol and xylitol (it should be recognized that the favoured conformation does not
necessarily have all the carbon atoms in the same plane):
H
OH
HO
HOCH
\ /
4"~c~'C~c jCH2OH
Hd
H
""~! C/ O H
HOCH2C/ C
,"kH H/kOH
/k H H/k CH20H
HO
D-Arabinitol
Xylitol
2-Carb-6. A n o m e r i c forms; use o f ~ and
2-Carb-6.1. The anomeric centre
The new centre of chirality generated by hemiacetal ring closure is called the anomeric centre. The two
stereoisomers are referred to as anomers, designated ~ or [~ according to the configurational relationship
between the anomeric centre and a specified anomeric reference atom.
2-Carb-6.2. The anomeric reference atom and the anomeric configurational symbol (ct or [3)
The anomeric reference atom is the configurational atom (see 2-Carb-4.2 and 4.3) of the parent, unless multiple
configurational prefixes (see 2-Carb-8.3) are used. If multiple configurational prefixes are used, the anomeric
reference atom is the highest-numbered atom of the group of chiral centres next to the anomeric centre that
is involved in the heterocyclic ring and specified by a single configurational prefix. In the t~ anomer, the
exocyclic oxygen atom at the anomeric centre is formally cis, in the Fischer projection, to the oxygen attached
to the anomeric reference atom; in the [3 anomer these oxygen atoms are formally trans.
The anomeric symbol t~ or 13, followed by a hyphen, is placed immediately before the configurational symbol
D or L of the trivial name or of the configurational prefix denoting the group of chiral carbon atoms that
includes the anomeric reference atom.
Examples:
H!OH 1
CH2OH
HOCIFH
--
.coil I
1
H ° C " /
.o
I
oH
H
CH2OH
CH2OH
--
HCO"I
OH
I
H
CH2OH
~-D-gluco
[~-D-gluco
c~-D-Glucopyranose
~-D-Glucopyranose
OH
H
f
MeOCH
I
HCOH
I
HOCH
I
~HOCH
oA
H
Me
I
H~.~H
CH2
I
O
H
HCOMe
HCOH
OH
k
~-L-arabino
Methyl (Z-L-arabinopyranoside
==~HOCH~
CH2
t
Ok
yjo~
m
r,,.°H
H ~
H
,H
,"~
OMe
OH
~-L-threo
Methyl I~-L-threofuranoside
19
CH20H
MeO~H
H?OH
OCH
H~O
.oc
n
"°c"/
H~OMe
H"
o
-
C.o
OMe
HO
O~H
i
HCOH'T~'~
~HCOH
CH2OH
I
H
CH2OH
H
OH
HCO
I
:==>HOCH
CH2OH
I
I
H
H
L-glycero-cz-D-manno
Methyl L-glycero-oc-D-manno-heptopyranoside
~-D-galacto
Methyl ~-D-galactofuranoside
( - MeOC--CH2OH
i
HOCH
i
HCOH
t
::=>~ HCO
I
CH2OH
r'.,.",
H ~
CH20H
OH H
[3-D-arabino
Methyl ~-D-fructofuranoside
HOC-COOMe
I
~m2
HCOH
I
AcNHCH
I
OCH
I
HCOH
I
:=:> HCOH
I
CHzOH
OH
HOC~o--~COOMe
A c N H ~
OH
D-glycero-~-D-galacto
Methyl 5-acetamido-3,5-dideoxy-D-glycero-f3-D-galacto-non-2-ulopyranosonate(see 2-Carb-14.2)
--4 denotes the anomeric reference atom; ~ denotes the configurational atom.
Note. For simple aldoses up to aldohexoses, and ketoses up to hept-2-uloses, the anomeric reference atom and the
configurational atom are the same.
2-Carb-6.3. M i x t u r e s of a n o m e r s
In solution, most simple sugars and many of their derivatives occur as equilibrium mixtures of tautomers. The
presence of a mixture of two anomers of the same ring size may be indicated in the name by the notation ix,13-,
e.g. tx,~-D-glucose. In formulae, the same situation can be expressed by separating the representation of the
ligands at the anomeric centre from the ct and 13 bonds [see examples (a) and (c)], or by use of a wavy line
[(b) and (d)] (particularly if hydrogen atoms are omitted).
Examples:
CH2OH
H H
O
HO~.~
'
H
H, OH
or
CH2OH
HO~0 ~ 0 ~ ~
H O . ~ h ~ O H OH
OH
(a)
(b)
oc,13-D-Glucopyranose
OPO32-
OPO32-
I
I
HO
(c)
H
HO
(d)
H
~,~-D-Fructofuranose 6-phosphate
20
2-Carb-6.4. Use of ~ and 15
The Greek letters ct and 15 are applicable only when the anomeric carbon atom has a lower locant than the
anomeric reference atom. In the case of dialdoses (cf. 2-Carb-9), some diketoses (cf. 2-Carb-1 I) and
aldoketoses (cf. 2-Carb- 12), ring closure is also possible in the other direction, i.e. of a carbonyl group with
a higher locant than the reference carbon atom with a hydroxy group having a lower locant. In this case, the
configuration of the anomeric carbon atom is indicated by the appropriate symbol R or S according to the
sequence rule (cf. Section E in [13]).
Examples:
6
CHO
HOCHjI/O
,k o,
s~ " 7 ' ~ , ~ O H
I
OH
H
H ~ ~
H
O--CMe 2
3
OH
(6R)-D-gluco-Hexodialdo-6,2-pyranose
(6S)-1,2-O-Isopropylidene-e~-D-gluco-hexodialdo1,4:6,3-difuranose
Note that locant numerals (potential carbonyl first) may be needed before the ring-size suffix in such cases.
2-Carb- 7. Conformation of cyclic forms*
2-Carb-7.1. The conformational descriptor
The conformation, i.e. the (approximate) spatial arrangement of the ring atoms of a monosaccharide in the
cyclic form, may be indicated by an italic capital letter designating the type of ring shape, and numerals,
distinguishing the variants. The conformational descriptor is joined to the end of the name of the monosaccharide by a hyphen.
Example:
CH20H t~
HO
OHoH
(z-D-Glucopyranose-4C1
Table 1. Conformations and their notations; some examples are shown in Chart III
Type of sugar
Conformation
Atoms of reference plane
Above plane
Aldofuranose
envelope
O-4,C-1,C-3,C-4
Aldofuranose
envelope
C- 1,C-2,C-4,O-4
C-3
Aldofuranose
twist
C-1 ,O-4,C-4
C-3
C-2
Aldofuranose
twist
C-3,C-4,O-4
C-2
Aldopyranose
chair
C-2,C-3,C-5,O-5
C-4
C-4
Pyranoid lactone chair
C-2,C-3,C-5,O-5
C-1
Aldopyranose
boat
O-5,C- 1,C-3,C-4
C-2,C-5
Aldopyranose
boat
C-2,C-3,C-5,O-5
Aldopyranose
skew
C-2,C-4,C-5,O-5
C-1
Aldopyranose
skew
C-1,C-3,C-4,C-5
Aldopyranose
half-chair
C- 1,C-2,C-3,C-4
C-1,C-2,C-3,C-4,O-5
C-5
Pyranoid lactone envelope
*
Belowplane
Notation Example
C-2
E2
1
3E
2
37"2
3
C-I
2TI
4
C- 1
4C1
5
IC4
6
2"5B
7
C-1,C-4
BI.4
8
C-3
IS3
9
C-2
0-5
2So
10
C-5
S-5
5Hs
11
5E
12
This is an abridged version of the document 'Conformational Nomenclature for Five- and Six-membered Ring
Forms of Monosaccfiarides and their Derivatives. Recommendations 1980 [3].
21
OCH3
H
HOCH~~
HOG.H2 .,~D__
......iiiiiiii~iiiiii:)'-::..H
H H~ii.."iiiiiiiiii)
!i.... OH
HO%~H
OH
H O C H 2 ~
H HO~,,,~2 OH
H
O"'"~C(CH3)2
1
(0H3)20~ O
O/
2'
~
0
3
2
CH2OH
H
OHH
H ~ ~ O ~
HOCH2~oJ~
H O ~ O H
H O ~ O H
H
H
H
4
5
__~ ~
H
H_I
O~
~ ~
............................0
H
H
H
6
CH2OH
o
"O
================================
"!i~i!iliiiiiii!iiiiiiii""
!
HOCH
0
Q.'.-?!:!:!!i:::iii::.
.
HO
.
H
7
HOx
H
8
H
H" ~.............
......• U OH'OH
H
/
10
1
3
5
7
9
" .o' % o .
OH
9
H s H
/
H
~
5 CH2OH
H'~
H
x
/~
O
\
OCH3
iiii!ii!i!i!iiiiiiii',i ii
/
HO
11
I .O
\"o . . . . . . . . . . . . . ./-/
12
MethylI]-D-arabinofuranoside-E2
2 C~-D-Arabinofuranose-3E
1,2-O-Isopropylidene-~-L-idofuranose-3T2
4 2,3-O-Isopropylidene-et-D-lyxofuranoseYT|
6 L-Glucono-1,5-1actone-IC4
0~-L-Arabinopyranose-4C!
Methyl2,6-anhydro-c~-D-altropyranoside-2'5B
8 1,4-Anhydro-et-D-allopyranose-Bl,4
1,2-O-Ethylidene-ct-D-glucopyranose-1S3
10 I]-L-Altropyranose-2So
5HS
11 Methyl2,3-anhydro-5-thio-l~-L-lyxopyranoside12 2,3-Dideoxy-D-erythro-hex-2-enono-l,5-1actone- 5E
Chart III. Drawings of the conformations listed in Table 1. The reference plane is stippled.
2-Carb-7.2. Notation of ring shape
The appropriate letters are as follows. Five-membered rings: E for envelope and T for twist; six-membered
rings: C for chair, B for boat, S for skew, H for half-chair, and E for envelope. Examples are given in Chart
HI.
2-Carb-7.3. Notation of variants
The variants are distinguished by the locants of those ring atoms that lie outside a reference plane (defined
below) and are listed for some examples in Table 1. The locants of ring atoms that lie on the side of the
reference plane from which numbering appears clockwise (i.e. the upper side in the normal Haworth
representation of furanoses and pyranoses) are written as superscripts and precede the letter; those that lie on
the other side are written as subscripts and follow the letter. Heteroatoms (e.g. O, 'S) are indicated by their
subscript or superscript atomic symbols. Table 1 gives the notations and Chart III some examples.
22
Six-membered rings
Chairs. The reference plane is defined by two parallel ring sides, so chosen that the lowest-numbered carbon
atom in the ring is exoplanar (examples 5 and 6).
Boats. The reference plane is defined by the two parallel 'sides' of the boat (examples 7 and 8).
Skews. Each skew form has two potential reference planes, containing three adjacent atoms and the remaining
non-adjacent atom. The reference plane is so chosen that the lowest-numbered carbon atom in the ring, or the
atom numbered next above it, is exoplanar, in that order of preference (examples 9 and 10).
Half-chairs. The reference plane is defined by the four adjacent coplanar atoms (example 11).
Envelopes. The reference plane is defined by the five adjacent coplanar atoms (example 12).
Five-membered rings
Envelopes. The reference plane is defined by the four adjacent coplanar atoms (examples 1 and 2).
Twists. The reference plane is defined by three adjacent ring-atoms, so chosen that the exoplanar atoms lie
on opposite sides of the plane (examples 3 and 4).
Note 1. Many of the possible conformations are not likely to contribute significantly to the chemistry of a particular
monosaccharide, but must be stabilized by formation of additional rings, as in anhydrides or other derivatives. Some
others may occur as transition-state intermediates.
Note 2. A more precise specification of conformation can be achieved by use of the Cremer-Pople puckering parameters
[221.
2-Carb-7.4. E n a n t i o m e r s
The conformational symbols for enantiomers are different. It is therefore important to state in the context
whether the D or the L form is under consideration. Enantiomers have the same reference plane (see
2-Carb-7.3), and it should be noted that the mirror image of O~-D-glucose-4C1 is t~-L-glucose-lC4.
/ H CH2OH
H
/
OH
mirrorplane
/
H
OH
HOH2C
H~@o'~H
H O ~ O H
H
H
Mirror images:C~-D-glucopyranose-4C1(upper)and oc-L-glucopyranose-lC4(lower)
2-Carb-8. Aldoses
2-Carb-8.1. Trivial n a m e s
The aldoses with three to six carbon atoms have trivial names which are given, together with the formulae in
the Fischer projection, in Chart I (2-Carb-2.2). (See also the alphabetical listing of trivial names in the
Appendix.)
The trivial names form the basis of the configurational prefixes (see 2-Carb-4.3).
2-Carb-8.2. Systematic names
Systematic names are formed from a stem name and a configurational prefix or prefixes. The stem names for
the aldoses with three to ten carbon atoms are triose, tetrose, pentose, hexose, heptose, octose, nonose, decose.
The chain is numbered so that the carbonyl group is at position 1.
23
The configuration of the CHOH groups of the sugar is designated by the appropriate configurational prefix(es)
from Chart I. When used in systematic names, these prefixes are always to be in lower case letters (with no
initial capital), and italicized in print. Each prefix is qualified by D or L (Chart I shows only the D structures).
Examples:
D-ribo-Pentosefor D-ribose
o-manno-Hexosefor D-mannose.
The trivial names are preferred for the parent sugars and for those derivatives where all stereocentres are
unmodified.
2-Carb-8.3. Multiple configurational prefixes
An aldose containing more than four chiral centres is named by adding two or more configurational prefixes
to the stem name. Prefixes are assigned in order to the chiral centres in groups of four, beginning with the
group proximal to C-1. The prefix relating to the group of carbon atom(s) farthest from C-1 (which may
contain less than four atoms) is cited first.
Examples:
HC=O
HOCH
HOCH
HCOH
HCOH
HOCH
HOCH
HOCH
CH2OH
HC=O
I
HCOHI }
HOCH
HCOH
I
HCOH
!
HC
OH
I
CH2OH
D-gluco
O-glycero
D-glycero-D-gluco-Heptose
D-gluco-D-glycero-heptose
t D-manno
L-ribo
L-ribo-D-manno-Nonose
D-manno-L-ribo-nonose
not
not
2-Carb-8.4. Multiple sets of ehiral centres
If sequences of chiral centres are separated by non-chiral centres, the non-chiral centres are ignored, and the
remaining set of chiral centres is assigned the appropriate configurational prefix (for four centres or less) or
prefixes (for more than four centres).
Example:
CHO
I
HCOH
71-t2
HCOH
I
L-tale
HCOH
I
q~
HOCH
I
HCOH
I
HOCH
L-three
I
CH2OH
3,6-Dideoxy-L-threo-L-talo-decose
Note 1. This convention is not needed for parent aldoses, only for deoxy aldoses, ketoses and similar compounds (see
2-Carb-10.4 and 2-Carb-11.2).
Note 2. Since all aldoses up to the hexoses have trivial names that are preferred, the systematic names apply only to the
higher aldoses. However, the configurational prefixes are also used to name ketoses (see below) and other monosaccharities.
2-Carb-8.5. Anomeric configuration in cyclic forms
For the specification of tx and 13 in cyclic forms see 2-Carb-6.
24
2-Carb-9. Dialdoses
Systematic names for individual dialdoses are formed from the systematic stem name for the corresponding
aldose (see 2-Carb-8.2), but with the ending 'odialdose' instead of 'ose', and the appropriate configurational
prefix (Chart I). A choice between the two possible aldose parent names is made on the basis of 2-Carb-2.2.2.
Examples:
CHO
[
HCOH
I
HOCH
I
HOCH
I
HCOH
I
CHO
CHO
I
HCOH
l
HOCH
I
CHO
galacto-Hexodialdose
L-thmo-Tetrodialdose
Note. The prefix 'meso-' could be included in the latter case, but it is not needed to define the structure.
If a cyclic form is to be named, the locants of the anomeric centre and of the carbon atom bearing the ring
oxygen atom must be given (in that order) (cf. 2-Carb-6.4). If there is more than one ring size designator, they
are placed in alphabetical order (e.g. furanose before pyranose).
Examples:
CHO
CHO
OH
(6 R)-D-gluco-Hexodialdo-6,2-pyranose
C~-D-gluco-Hexodialdo-1,5-pyranose
HO
0~~00Me
OH
OH
Methyl c~-o-gluco-hexodialdo-6,34uranose-1,5-pyranoside
2-Carb-lO. Ketoses
2-Carb-10.1. Classification
Ketoses are classified as 2-ketoses, 3-ketoses, etc., according to the position of the (potential) carbonyl group.
The locant 2 may be omitted if no ambiguity can arise, especially in a biochemical context.
2-Carb-10.2. Trivial names
Ketoses with three to six carbon atoms are shown in Chart IV, with trivial names (and three-letter abbreviations) in parentheses. (See also the alphabetical listing of trivial names in the Appendix.)
The trivial names 'D-erythrulose' for D-glycero-tetrulose, 'D-ribulose' for D-erythro-pent-2-ulose, and 'D-xylulose' for D-threo-pent-2-ulose contain stereochemical redundancy and should not be used for naming
derivatives. Sedoheptulose is the accepted trivial name for D-altro-hept-2-ulose.
2-Carb-10.3. Systematic names
The systematic names are formed from the stem name and the appropriate configurational prefix.
The stem names are formed from the corresponding aldose stem names (2-Carb-8.2) by replacing the ending
'-ose' with '-uiose', preceded by the locant of the carbonyl group, e.g. hex-3-ulose. The chain is numbered
so that the carbonyl group receives the lowest possible locant. If the carbonyl group is in the middle of a chain
with an odd number of carbon atoms, a choice between alternative names is made according to 2-Carb-2.2.2.
25
Note. In Chemical Abstracts Service (CAS) usage the Iocant for the carbonyl group precedes the stem name, e.g.
3-hexulose.
For examples see 2-Carb-10.4.
CH2OH
C=O
i
CH2OH
1, 3-Dihydroxyacetone
CH2OH
c=o
HCOH
i
CH2OH
D-glycero -Tetrulose
('D-Erythrulose')
CH2OH
CH2OH
c=o
c=o
HCOH
i
HCOH
i
CH2OH
D-erythro-Pent-2-ulose
('D-Ribulose';D-Rul)
HOCH
HCOH
CH2OH
D-threo-Pent-2-ulose
('O-Xylulose';D-Xul)
CH2OH
c=o
HCOH
HCOH
HCOH
CH2OH
D-ribo-Hex-2-ulose
(D-Psicose;D-Psi)
CH2OH
c:o
HOCIH
HCOH,
HCOH
CH2OH
CH2OH
c:o,
HCOH
HOCH,
HCOH
CH2OH
CH2OH
c:o
HOCH
HOCH
HCOH
CH2OH
D-arabino-Hex-2-ulose D-xylo-Hex-2-ulose D-lyxo-Hex-2-ulose
(D-Fructose;D-Fru) (D-Sorbose;D-Sor) (D-Tagatose;D-Tag)
C h a r t IV. Structures, with systematic and trivial names, of the 2-ketoses with three to six carbon atoms
2-Carb-10.4. Configurationai prefixes
For 2-ketoses, configurational prefixes are given in the same way as for aldoses (see 2-Carb-8.2 and
2-Carb-8,3).
Examples:
CH20H
I
CH2OH
I
C=O
I
HOCH
I
HCOH
I
HOCH
I
CH2OH
C=O
I
HOCH
I
HCOH
I
HCOH
I
HCOH
I
CH2OH
L-~lo-l-lex-2-ulose
D-a/tro-Hept-2-ulose
(L-Sorbose)
(D-Sedoheptulose)
H2OH
C=O
I
HOCH
I
HOCH
I
HCOH
I
HCOH
I
HOCH
I
CH2OH
L-glycero-D-manno-Oct-2-ulose
CH20H
-~'~CH2OH
OH
OH
D-altro-Hept-2-ulopyranose
26
For ketoses with the carbonyl group at C-3 or a higher-numbered carbon atom, the carbonyl group is ignored
and the set of chiral centres is given the appropriate prefix or prefixes according to Chart I (cf. 2-Carb-8.4).
Examples:
CH20 H
H2OH
CH2OH
HCOH
I
C:O
I
C:O
I
C:O
I
HCOH
I
HOCH
I
HOCH
I
HCOH
I
HCOH
I
HOCH
I
CH2OH
I
CH2OH
CH2OH
D-xy/o-Hex-3-ulose
not L-xy/o-hex-4-ulose
D-arabino-Hex-3-ulose
CH20 H
L-gluco-Hept-4-ulose
not D-gulo-hept-4-ulose
CH2OH
t
HOCH
HCOH
HOCH
D-allo -
HCOH
HCOH
HCOH
HOCH
I
HCOH
I
HCOH
I
I
HOCH
HCOH
C=O
HOCH
L-three -
L-erythro -
HOCH
CH2OH
L-threo-D-allo-Non-3-ulose
L-gluco -
C=O
HOCH
HOCH
CH2OH
L-erythro-L-gluco-Non-5-ulose
not D-threo-D-allo-non-5-ulose
2-Carb-l l. Diketoses
2-Carb-11.1. Systematic names
The systematic name of a diketose is formed by replacing the terminal '-se' of the stem name by '-diulose'.
The locants of the (potential) carbonyl groups must be the lowest possible and appear before the ending. The
stem name is preceded by the appropriate configurational prefix. If there is a choice of names, a decision is
made on the basis of 2-Carb-2.2.2. In cyclic forms, locants may be needed for the positions of ring closure;
that of the (potential) carbonyl group is cited first.
Examples:
H2OH
CH2OH
C=O
I
I
C--O
HCOH
I
I
HCOH
HOCH
I
I
HOCH
HCOH
I
I
C:O
C:O
CH2OH
CH2OH
L-threo-Hexo-2,5-diulose
meso-xylo-Hepto-2,6-diulose
I
t
2-Carb-ll.2. Multiple sets of chiral centres
If the carbonyl group(s) divides the sequence of chiral centres, the configurational prefixes are assigned in
the normal manner (see 2-Carb-8.4) for all chiral centres; the non-chiral centres are ignored.
Examples:
?H20 H
HCOH
i
CH20 H
HOCH
I
C--O
Hop.
I
C=O
O
?.2o.
i
CI : O
HCOH
I
CH20 H
D-threo-Hexo-2,4-diulose
OO ~H , ~ ~
O
I
o--o
i
HOCHI
H
H
C~-D-threo-Hexo-2,4-diulo-2,5-furanose
HOCH
I
CH20 H
L-altro-Octo-4,5-diulose
not L-talo-octo-4,5-diulose
27
CH2OH
HOCH
C--O
HCOH
D-ido HOCH
C:O
HCOH
HCOH D-glyceroCHeOH
?H20H
C:O
HOCH }
HOCH
D-manno
HCOH
HCOH
C=O
L-glyceroHOCH
CHzOH
D-glycero-D-ido-Nono-3,6-diulose
L-glycero-o-manno-Nono-2,7-diulose
2-Carb-12. Ketoaldoses (aldoketoses, aldosuloses)
2-Carb-12.1. Systematic names
Names of ketoaldoses are formed in the same way as those of diketoses, but with use of the termination '-ulose'
in place of the terminal '-e' of the corresponding aldose name (2-Carb-8.2). The carbon atom of the (potential)
aldehydic carbonyl group is numbered 1, and this locant is not cited in the name. The locant of the (potential)
ketonic carbonyl group is given (as an infix before '-ulose') unless it is 2; it may then be omitted (in this text,
this locant is always retained for the sake of clarity). In cyclic forms, locants may be needed for the positions
of ring closure; that of the (potential) carbonyl group is cited first. The position of the ring-size designator
(e.g. pyrano) depends upon which carbonyl group is involved in ring formation (see examples).
Examples:
f
MeO?H
CHO
f
HOCH
,
HCOH!
o=o
HCOH
'
HCOH
i
CH2OH
O
2]
HO-~'~
?=
HCO
I
CH2OH
D-arabino-Hexos-3-ulose
OMe
OH
Methyl [J-D-xylo-hexopyranosid-4-ulose
•
1
I MeO?-C,O
/
HOCIH
yfO
?Me
-=
/"c°H
I
CH2OH
Hoo"21----# cHo
OH
H
Methyl ~-L-xylo-Hexos-2-ulo-2,5-furanoside
2-Carb-12.2. 'Dehydro' names
In a biochemical context, the naming of aldoketoses as 'dehydro' aldoses is widespread. Thus D-xylohexopyranos-4-ulose would be termed 4-dehydro-D-glucose. This usage of 'dehydro' can give rise to names
which are stereochemically redundant, and should not be employed for naming derivatives.
Note. In Enzyme Nomenclature [23] dehydro names are used in the context of enzymic reactions. The substrate is
regarded as the parent compound, but the name of the product is chosen according to the priority given in 2-Carb-2.2.
Examples:
D-Glucose + 02 = 2-dehydro-D-glucose + H202 (EC 1.1.3.10)
Sucrose + acceptor = [3-D-fructofuranosyl3-dehydro4x-D-allopyranoside+ reduced acceptor (EC 1.1.99.13)
L-Sorbose + NADP + = 5-dehydro-D-fructose + NADPH (reaction of sorbose dehydrogenase, EC 1.1.1.123)
28
2-Carb-13. Deoxy sugars
2-Carb-13.1. Trivial n a m e s
Several deoxy sugars have trivial names established by long usage, e.g. fucose (Fuc), quinovose (Qui) and
rhamnose (Rha). They are illustrated here in the pyranose form. These names are retained for the unmodified
sugars, but systematic names are usually preferred for the formation of names of derivatives, especially where
deoxygenation is at a chiral centre of the parent sugar. (See also the alphabetical listing of trivial names in
the Appendix.)
Examples:
OH
oH~O
OH
CH3
H
OH
H O ~
OH
OH
C~-L-Fucopyranose
6-Deoxy-~t-L-galactopyranose
!3-D-QUinovopyranose
6-Deoxy-13-D-glucopyranose
H O ~ o
L-Rhamnopyranose
6-Deoxy-L-mannopyranose
H
OH
2,6-Dideoxy-~-o-ribo-hexopyranose
(p-Digitoxopyranose)
HO
OH
OH
3,6-Dideoxy-I~-D-xylo-hexopyranose
(13-Abequopyranose)
3,6-Dideoxy-~-D-arabino-hexopyranose
(l~-Tyvelopyranose)
Other trivial names that have been used include ascarylose for 3,6-dideoxy-L-arabino-hexose, colitose for
3,6-dideoxy-L-xy/o-hexose and paratose for 3,6-dideoxy-D-ribo-hexose.
Note. Sugars with a terminal CH3 group should be named as o3-deoxysugars, as shown above, not C-methyl derivatives.
2-Carb-13.2. Names derived from t r i v i a l n a m e s of sugars
Use of 'deoxy-' in combination with an established trivial name (see Charts I and II) is straightforward if the
formal deoxygenation does not affect the configuration at any asymmetric centre. However if 'deoxy' removes
a centre of chirality, the resulting names contain stereochemical redundancy. In such cases, systematic names
are preferred, especially for the naming of derivatives.
Note. The names 2-deoxyribose (for 2-deoxy-D-erythro-pentose)and 2-deoxyglucose (for 2-deoxy-D-arabino-hexose)
are often used.
OPOa2I
HI~
HO
~
H,OH
H
2-Deoxy-D-erythro-pentofuranose5-phosphate
2-Carb-13.3. Systematic names
The systematic name consists of the prefix 'deoxy-', preceded by the locant and followed by the stem name
with such configurational prefixes as necessary to describe the configuration(s) at the asymmetric centres
29
present in the deoxy compound. Configurational prefixes are cited in order commencing at the end farthest
from C- 1. 'Deoxy' is regarded as a detachable prefix, i.e. it is placed in alphabetical order with any substituent
prefixes.
Note. The treatment of 'anhydro' (see 2-Carb-26), 'dehydro' (see 2-Carb-17.3) and 'deoxy' as detachable prefixes
follows long-standing practice in carbohydrate chemistry, but is in conflict with [14] (p. 12).
Examples:
CHO
i
HCH
I
HCOH
i
HCOH
I
HCOH
CH2OH0
HO~OH
OH
CH2OH
I
2-Deoxy-D-ribo-hexose not 2-deoxy-D-allose
4- Deoxy-13-D-xy/o-hexopyranose
not 4-deoxy-J3-D-galactopyranose
HCOH
I
HCH
HCOHI
HCOH
I
HC
I
HCOH
CH3
C:O
HOCH
HCOH
HCOH
HCOH
HOCH
CH2OH
CH2OH
I
HOCH
O
J
CH2OH
I
HHHO~ . ~ O
OH
H
H
1-Deoxy-L-glycero-D-altro-oct-2-ulose
2-Deoxy-o~-D-allo-heptopyranose
Bzo
N3
OMe
Methyl 3-azido-4-O-benzoyl-6-bromo-2,3,6-trideoxy-2-fluoro-a-D-allopyranoside
If the CH2 group divides the chiral centres into two sets, it is ignored for the purpose of assigning a
configurational prefix; the prefix(es) assigned should cover the entire sequence of chiral centres (see
2-Carb-8.4).
Examples:
CH2OH
I
HOCH
i
C=O
I
HCOH
I
CH2
i
HCOH
I
CH2OH
CHO
i
HCOH
t
CH2
i
HCOH
t
HCOH
I
CH2OH
3-Deoxy-o-ribo-hexose
not 3-deoxy-D-erythrO-D-glycero-hexose
5-Deoxy-D-arabino-hept-3-ulose
not 5-deoxy-D-glycero-D-glycero-L-glycero-hept-3-ulose
CH2OH
C--O
HOCH
HCOH
HOCH
CH2
HOCH
CHzOH
6-Deoxy-L-g/uco-oct-2-ulose
not 6-deoxy-L-glycero-L-xylo-oct-2-ulose
30
If the anomeric hydroxy group is replaced by a hydrogen atom, the compound is named as an anhydro alditol
(2-Carb-26).
2-Carb-13.4. Deoxy alditols
The name of an aldose derivative in which the aldehyde group has been replaced by a terminal CH3 group is
derived from that of the appropriate alditol (see 2-Carb-19) by use of the prefix 'deoxy-'.
Examples:
CH31
HOCH
I
HCOH
I
HCOH
[
CH2OH
1
~
~H2OH
HOCH
I
HOCH
I
HCOH
5
I
CH 3
1-Deoxy-D-arabinitol
CH2OH
HOCH
I
HCOH
I
HCOH
I
CH 3
1
~
CH
31
HOCH
I
HOCH
I
HCOH
I
CH2OH
5
5-Deoxy-D-arabinitol
not 1-deoxy-D-lyxitol
not 5-deoxy-D-lyxitol
The alditols from fucose and rhamnose are frequently termed fucitol and rhamnitol (see 2-Carb-19.1).
2-Carb-14. Amino sugars
2-Carb-14.1. General principles
The replacement of an alcoholic hydroxy group of a monosaccharide or monosaccharide derivative by an
amino group is envisaged as substitution of the appropriate hydrogen atom of the corresponding deoxy
monosaccharide by the amino group. The stereochemistry at the carbon atom carrying the amino group is
expressed according to 2-Carb-8.2, with the amino group regarded as equivalent to OH.
Some examples of N-substituted derivatives are given here; for a detailed treatment see 2-Carb-25.
2-Carb-14.2. Trivial names
Accepted trivial names are as follows.
D-Galactosamine for 2-amino-2-deoxy-D-galactose
D-Glucosamine for 2-amino-2-deoxy-D-glucose
D-Mannosamine for 2-amino-2-deoxy-D-mannose
D-Fucosamine for 2-amino-2,6-dideoxy-D-galactose
D-Quinovosamine for 2-amino-2,6-dideoxy-D-glucose
Neuraminic acid for 5-amino-3,5-dideoxy-D-glycero-D-galacto-non-2-ulosonic acid
Muramic acid for 2-amino-3-O-[(R)- 1-carboxyethyl]-2-deoxy-D-glucose.
In the last two cases the trivial name refers specifically to the D enantiomer. (See also the alphabetical listing
of trivial names in the Appendix.)
Such names as 'bacillosamine' for 2,4-diamino-2,4,6-trideoxy-D-glucose and 'garosamine' for 3-deoxy-4-Cmethyl-3-methylamino-L-arabinose are not recommended, as they imply replacement of OH by NH2 in a
nonexistent parent sugar.
Examples:
H O ~ o
H
2-Amino-2-deoxy-D-glucopyranose (D-glucosamine).
31
HOOC-COH
CH2
HCOH
AcNHCH
OCH
reference
atom ~ HCOH
HCOH
CH2OH
H
Ac
OH
K HCOH
=-
___
t'lX CH2OH
OH
OH
OOH
/OH
COOH
HOCH~o-~OH
AcNH~ ' ~ , ~ , , , ~
OH
H
5-Acetamido-3,5-dideoxy-D-glycero-o~-D-galacto-non-2-ulopyranosonic acid
(N-acetyl-c~-neuraminic acid, ~-Neu5Ac),
drawn in three ways (note that C-7 is the anomeric reference atom)
CH2OH
H
HCOOH
LMe./.,, H
OH
HO " ~ O
I
H
NH2
2-Amino-3-O-[(R)-l-carboxyethyl]-2-deoxy-l]-D-glucopyranose (I]-muramic acid)
For examples with nitrogen in the ring, see 2-Carb-34.1.
2-Carb-14.3. Systematic names
The compounds are named by use of a combination of 'deoxy-' and 'amino-' prefixes. When the complete
name of the derivative includes other prefixes, 'deoxy-' takes its place in the alphabetical order of detachable
prefixes.
Examples:
HOCH2--"~'--~O . . ~ OH
HO~ _ _ . . . . , ' ~ NHMe
OH
2-Deoxy-2-methylamino-L-glucopyranose
CH3
,~
OAc
p./-..J...Ac
I OAc
OH
4,6-Dideoxy-4-formamido-2,3-di-O-methylD-mannopyranose
OAc
2-Acetamido-1,3,4-tri- O-acetyl-2,6-dideoxyC~-L-galactopyranose
When the amino group is at the anomeric position, the compound is normally named as a glycosylamine (see
2-Carb-33.6).
2-Carb-15. Thio sugars and other chalcogen analogues
Replacement of a hydroxy oxygen atom of an aldose or ketose, or of the oxygen atom of the carbonyl group
of the acyclic form of an aldose or ketose, by sulfur is indicated by placing the prefix 'thio', preceded by the
appropriate locant, before the systematic or trivial name of the aldose or ketose.
Replacement of the ring oxygen atom of the cyclic form of an aldose or ketose by sulfur is indicated in the
same way, the number of the non-anomeric adjacent carbon atom of the ring being used as locant.
Selenium and tellurium compounds are named likewise, by use of the prefix 'seleno' or 'telluro'.
Sulfoxides (or selenoxides or telluroxides) and sulfones (or selenones or tellurones) may be named by
functional class nomenclature [ 13].
32
Note. The appropriate prefix is thio, not thia; the latter is used in systematic organic chemical nomenclature to indicate
replacement of CH2 by S.
Examples:
A c o ~CHaOAc
- - ~n
H°
AcO~SH
OAc
2,3,4,6-Tetra-O-acetyl-1-thio-13-D-glucopyranose
5-Thio-[3-D-glucopyranose
HOI~,/Se~
H?OAc /
AcO~----~
o.
OH
H~SMe1
CH2OTr,--,
CH2OH
IH
~OH
H~
H ~
H
OH
H~OMe 1
.,~o~-- /
_-()Me
HOCHHI~JSel
i
CH20H
I
CH2OTr
Methyl 2,3,4-tri-O-acetyl-1-thio-6-O-trityl-cc-D-glucopyranoside Methyl 4-seleno-~-D-xylofuranoside
CH2OH
.s
HO~OH
OH
o4"Se'~ph
4-Thio-I~-D-galactopyranose
c(-D-Glucopyranosylphenyl (R)-selenoxide
r
H O ~ . ~HS eH?
~ ~~?H2OH ~_
H ~
HO
H
Aco....~c, 2OAc
/
HOCH2--COMe
HOCHHcoHI/
OMe
AcO~ " ~ '"~- -" s" ~ S E t
AcO?H/
HCS---J
OAc
HCOAc
I
CH2OAc
Ethyl 3,4,6,7-tetra-O-acetyl-2-deoxy-l,5-dithio-c(-Dgluco-heptopyranoside
HCSe]
-~J
I
CH2OH
Methyl 5-seleno-c~-o-fructofuranoside
_=
9"2 /
H?OAc /
Note. It is common practice in carbohydrate names to regard 'thio' as detachable, and therefore alphabetized with any
other prefixes.
2-Carb-16. Other substituted monosaccharides
2-Carb-16.1. Replacement of hydrogen at a non-terminal carbon atom.
The compound is named as a C-substituted monosaccharide. The group having priority according to the
Sequence Rule ([ 13], Section E) is regarded as equivalent to OH for assignment of configuration. Any potential
ambiguity (particularly when substitution is at the carbon atom where ring formation occurs) should be
avoided by use of the R,S system to specify the modified stereocentre.
Examples:
CH2OAc O
-- CH2OH O
A c O ~
H O ~
OH
2- C-Phenyl-c~-D-glucopyranose
AcNH I
F
2-C-Acetamido-2,3,4,6-tetra-O-acetyl-~-D-mannopyranosyl
fluoride
AcO
COOH O
OAc
(5R)-1,2,3,4-Tetra-O-acetyl-5-bromo-c~-D-X34o-hexopyranuronic
acid
or 1,2,3,4-tetra-O-acetyl-5-breme-[3-t.-idopyranuronic
acid
33
2-Carb-16.2. Replacement of OH at a non-terminal, non-anomeric carbon atom
The compound is named as a substituted derivative of a deoxy sugar. The group replacing OH determines the
configurational description. Any potential ambiguity should be dealt with by the alternative use of the R,S
system to specify the modified stereocentre.
Examples:
H O ~ o
H
2-Deoxy-2-phenyl-a-D-glucopyranose or 2-deoxy-2-C-phenyl-ot-D-glucopyranose
or (2R)-2-deoxy-2-phenyl-o~-D-arabino-hexopyranose
ONO2
2,3-Diazido-4-O-benzoyl-6-bromo-2,3,6-trideoxy-ct-D-mannopyranosyl nitrate
Note. Use of the symbol C- is essential only in cases of potential ambiguity, to make clear that substitution is at carbon
rather than at a heteroatom (cf. 2-Carb-18.2); however, it may also be used for emphasis.
2-Carb-16.3. Unequal substitution at a non-terminal carbon atom
The compound is named as a disubstituted deoxy sugar. Configuration is determined by regarding the
substituent having priority according to the Sequence Rule ([13], Section E), as equivalent to OH. Any
potential ambiguity should be dealt with by the alternative use of the R,S system to specify the modified
stereocentre.
Example:
HO CH2OH O\
H° 1--r sr
OH
(2R)-2-Bromo-2-chloro-2-deoxy-o~-o-arabino-hexose
or 2-bromo-2-chloro-2-deoxy-et-D-glucopyranose
(Br has priority over CI)
2-Carb-16.4. Terminal substitution
If substitution at the terminal carbon atom of the carbohydrate chain creates a chiral centre, the stereochemistry
is indicated by the R,S system.
Example:
CHO
I
HCOH
I
HOCH
I
COH
Ph
(5 R)-5-C-Cyclohexyl-5-C-phenyI-D-xylose
Note. A monosaccharide with a terminal methyl group is named as a deoxy sugar, not as a C-methyl derivative.
Substitution of aldehydic H by a ring or ring system is indicated simply with a C-substituent prefix.
34
Examples:
Ph
I
C=O
I
HCOH
I
HOCH
I
HCOH
I
HCOH
H
O
~
o
H
Ph
I
CH2OH
1-O-PhenyI-D-glucose
not 1-C-phenyI-D-gluco-hex-1-ulose
1- C-Phenyl-~-D-glucopyranose
2-Carb-16.5. Replacement of carbonyl oxygen by nitrogen (imines, oximes, hydrazones, osazones
etc.)
The imino analogue of a monosaccharide may be named as an imino-substituted deoxy alditol.
Example:
CH=NMe
HCOH
I
HOCH
I
HCOH
I
CH2OH
1-Deoxy-1 -(methylimino)-D-xylitol
Oximes, hydrazones and analogues are named directly as oxime or hydrazone derivatives etc.
Example:
CH=N--NHPh
1
HCOH
I
HOCH
I
HCOH
I
HCOH
I
CH2OH
D-Glucose phenylhydrazone
The vicinal dihydrazones formed from monosaccharides with arylhydrazines have been called arylosazones,
but are preferably named as ketoaldose bis(phenylhydrazone)s
Example:
CH ~N--NHPh
I
CH=N--NHPh
I
HOCH
i
HCOH
I
HCOH
I
CH2OH
g-arabino-Hexos-2-ulose bis(phenylhydrazone)
or D-arabino-hex-2-ulose phenylosazone
The triazoles formed on oxidising arylosazones (commonly called osotriazoles) may also be named as
triazolylalditols.
Hc~N.,
I
NPh
C~ "
I~N
HOCH
I
HCOH
I
HCOH
I
CH2OH
D-arabino-Hexos-2-ulose phenylosotriazole
or (1 R)-I -(2-phenyl-2H-1,2,3-triazol-4-yl))-D-erythritol
or 2-phenyl-4-(o-arabino-1,2,3, 4-tetrahydroxybutyl)-2H-1,2,3-triazole
35
2 - C a r b - 1 6 . 6 . I s o t o p i c substitution a n d isotopic labelling
Rules for designating isotopic substitution and labelling are given in [13] (Section H). Parentheses indicate
substitution; square brackets indicate labelling. The locant U indicates uniform labelling.
Examples:
D-(1-13C)Glucose (substitution)
o-(2-2H)Mannose (substitution)
L-[U-14C]Arabinose (labelling)
D-[1-3H]Galactose (labelling)
When isotopic substitution creates a centre of chirality, configuration is defined as for other types of
substitution (see 2-Carb- 16.1 to 2-Carb- 16.4).
Example:
CHO
I
2HCH
I
CH2OH
O
HOH O ~ ~ ~
HOCH
I
HCOH
18F
I
OH
CH2OH
2-Deoxy-D-(2-2H)lyxose (substituted)
or (2S)-2-deoxy-D-threo-(2-ZH)pentose
2-Deoxy-2-[18F]fluoro-D-glucose (labelled)
or (2R)-2-deoxy-2-[ 18F]fluoro-D-arabino-hexose
2-Carb-I 7. Unsaturated monosaccharides*
2-Carb-17.1. General principles
This section relates to the introduction of a double or triple bond between two contiguous carbon atoms of
the backbone chain of a monosaccharide derivative. A double bond between a carbon atom of the backbone
chain and an atom outside that chain, or a double or triple bond between two carbon atoms outside the backbone
chain, will be treated according to the normal rules of organic nomenclature [ 13,14].
2-Carb-17.2. Double bonds
Monosaccharide derivatives having a double bond between two contiguous carbon atoms of the backbone
chain are named by inserting, into the name for the corresponding fully saturated derivative, the infix 'x-en'.
The infix is placed directly after the stem name that designates the chain length of the sugar. The locant x is
the lower-numbered carbon atom involved in the double bond. Steric relations at a double bond are designated,
if necessary, by the standard stereosymbols '(Z)-' and '(E)-' preceding the whole name ([13], Section E). For
multiple double bonds, infixes such as 'x,y-dien' are used (preceded by an inserted 'a' for euphony).
Note 1. The term 'glycal' is a non-preferred, trivial name for cyclic enol ether derivatives of sugars having a double
bond between carbon atoms 1 and 2 of the ring. It should not be used or modified as a class name for monosaccharide
derivatives having a double bond in any other position.
Note 2. Following the principle of first naming the saturated derivative, compounds having a C=CR-O- group as part
of a ring system are named as unsaturated derivatives of anhydro alditols if R is hydrogen or carbon; if R is a halogen,
chalcogen, or nitrogen-family element, the resulting name is that of a glycenose or glycenosyl derivative.
Note 3. The symbols (Z)- and (E)- may be omitted when the double bond is located within a ring system of six atoms
or less, as steric constraints in such systems normally permit only one form.
Examples:
CH2OH
H
H
H
1,5-Anhydm-2-deoxy-D-arabino-hex-l-enitol (non-preferred trivial name D-glucal)
*
This is based on the 1980 recommendations [5]. Some examples have been omitted.
36
)oMe
HOCHo .O
H
Methyl
HOCH2
O__ /
I~
~H H
H
2-deoxy-D-threo-pent-l-enofuranoside
x
H
t -(2-Deoxy-D-threo-pent-I -enofuranosyl)uracil
H
H
CI
Ac
AcO
H
3,4-DPO-acetyl-2-deoxy-D-erl~hro-p,ent-1-enopyranosyl chloride
CH2OH
H
H~/
I
f
OH
2,6-Anhydro-1
(alphabetic preference over
CH2
H
-deoxy-D-altro-hept-l -enitol
2,6-anhydro-7-deoxy-D-falo-hept-6-enitol)
CH2
ii
CH
i
HOCH
i
HCOH
I
HCOH
i
CH2OH
OAc
i
H..-C~ C .-OAc
I
HCOAC
I
HCOAc
I
CH2OAc
1,2-Dideoxy-D-arabino-hex-l-enitol
(Z)-1,2,3,4,5-Penta-O-acetyI-D-erythro-pent-1 -enitol
H
MeO...C/OMe
ii
CH
I
HOCH
I
HCOH
I
CH2OH
I
Aco.-C~ C .-OAc
i
HCOAc
HCOAc
i
CH2OAc
(E)-1,2,3,4,5-Penta-O-acetyI-D-erythro-pent-l-enitol
2-Deoxy-D-threo-pent-l-enose dimethyl acetal
OH2
II
CH
I
HOCH
I
CH
II
CH
I
HCOH
I
HCOH
I
CH2OH
H.COH
CH20H
HO?, UH
H
H
2,3-Dideoxy-~-D-erythro-hex-2-enopyranose
1,2,4,5-Tetradeoxy-D-arabino-octa-1,4-dienitol
CH2OH
HO
OH
1,5-Anhydro-4-deoxy-D-erl~hro-he×-4-enitol
(enantiomeric precedence over 2,6-anhydro-a-deoxy-L-er~hro-hex-2-enitol)
37
H
HO ~
CH2OH
H
H
Methyl 3,4-dideoxy-~-o-glycero-hex-3-en-2-ulopyranoside
CH2OH
o
H
H
H
H
2,3-Dideoxy-o~-D-glycero-hex-2-enopyranos-4-ulose
CH2OH
o~O~
OMe
~
CH2OH
H
H
Mothyl 3,4-dideoxy-~-D-glycero-hept-3-en-2-ulopyranosid-5-ulose
O
H
r---i \
H
O--CMe2
5-Deoxy-1,2-O-isopropylidene-[~-L-threo-pent-4-enofuranose
CH2
II
HC O H
°i o
H
O-CMe2
5,6-Dideoxy-1,2-O-isopropylidene-o~-D-xylo-hex-5-enofuranose
2-Carb-17.3. Triple bonds and cumulative double bonds
Monosaccharide derivatives having a triple bond or cumulative double bonds in the backbone chain are named
by the methods of 2-Carb-17.2, with the infix 'n-yn' for a triple bond and infixes such as 'i,j-dien' for
cumulative double bonds.
Note. This approach was not included in [5].
Alternatively they can be named on the basis of the corresponding fully saturated sugar by using the
appropriate number of dehydro and deoxy prefixes (deoxy operations are regarded as formally preceding
dehydro operations). The prefixes are placed in alphabetical order before the stem name.
Examples:
CH2OH
H OH
(Z)-1,7-Anhydro-2,5,6-trideoxy-D-xylo-oct-5-en-1-ynitol
or (Z)-1,7-anhydro-1,1,2,2-tetradehydro-2,5,6-trideoxy-o-xylo-oct-5-enitol
38
OMe
i
c
Ill
c
I
HOCH
I
HCOH
I
CH2OH
2-Deoxy-l-O-methyI-D-threo-pent-l-ynitol
or 1,1,2,2-tetradehydro-2-deoxy-l-O-methyI-D-threo-pentitol
HC---C---CH2
( ~--.--O
Me2C L . .H~ ~'~t_.~,~
H
.H/~
~'~L~
~ Me2CO ~ ~ O
H
O--CMe 2
-=
\CMe2
.O
...O ~ , . ,O
, O
O
Me2CI
.....O
I 2
/CMe
6,7,8-Trideoxy-1,2:3,4-di-Gqsopropylidene-e~-D-galacto-octa-6,7-dienopyranose
or 6,7,7,8-tetradehydro-6,7,8-trideoxy-1,2:3,4-di-Oqsopropylidene-~-D-galacto-octopyranose
OAc
I
c
III
H~.-~
H
6H
OH
6- O-Acetyl-5-deoxy-c~-D-.~oflo-hex-5-ynofuranose
or 6-O-acetyl-5,5,6,6-tetradehydro-5-deoxy-e{-D-xylo-hexofu ranose
CH 3
C=O
I
c
II1
C O H
I
H
I\
O-CMe2
5,6,8-Trideoxy-1,2-O-isopropylidene-~-D-xylo-oct-5-ynofuranos-7-ulose
or 5,5,6,6-tetradehydro-5,6,8-trideoxy-1,2-O-isopropylidene-(~-D-xylo-octofuranos-7-ulose
2-Carb-18. Branched-chain sugars*
2-Carb-18.1. Trivial n a m e s
Several branched monosaccharides have trivial names, some established by long usage. Examples are given
below, together with systematic names for the (cyclic or acyclic) forms illustrated. (See also the alphabetical
listing of trivial names in the Appendix.) Enantiomers of the sugars listed should be named systematically.
Examples:
H
H
O
OHH
OH
OH
Hamamelose
2- C-(Hydroxymethyl)-D-ribopyranose
*
This is a modified form of the 1980 recommendations [4]. Priority is now given to naming cyclic forms, since in
most cases branched-chain monosaccharides will form cyclic hemiacetals or hemiketals.
39
OH
H
O
~
CH3
Cladinose
2,6-Dideoxy-3-C-methyl-3-O-methyl-L-n'bo-hexopyranose
H
O
H3C'C O ~ ~
H, OH
OH OH
Streptose
5-Deoxy-3-C-formyI-L-lyxofuranose
CH3
OH
6-Deoxy-3-C-methyI-D-mannopyranose
(Evalose)
CH3-'7~-~ O~ 7 "~OH
MeOO z N ~ ' ~ ~
2,3,6-Trideoxy-3-C-methyl-4-O-methyl-3-nitro-L-arabino-hexopyranose
(Evemitrose)
OH
MeNH~"~OH
OH
3-Deoxy-4-C-methyl-3-methylamino-L-arabinopyranose
(Garosamine)
CHO
i
HCOH
I
HOCH2--?-CH2OH
ON
D-Apiose (Api)
3-C-(Hydroxymethyl)-D-glycero-tetrose
Note. For the cyclic forms of apiose, systematic names are preferred, e.g.
.H j O ~
HO
H
OH
3-C-(Hydroxymethyt)-ct-D-erythrofuranose
[The name ~-D-erythro-apiofuranose is ambiguous; Chemical Abstracts Service (CAS) uses the trivial name o-apioc~-o-furanose; Beilstein gives (3R)-o~-D-apiofuranose]
40
2-Carb-18.2. S y s t e m a t i c names
A branched-chain monosaccharide is named as a substituted parent unbranched monosaccharide, as outlined
in 2-Carb- 16.1 to 2-Carb- 16.4.
Note. C-Locants are essential only where there is potential ambiguity, to make clear whether substitution is at carbon
or at a heteroatom (cf. 2-Carb-16); however, they may also be used for emphasis.
2-Carb-18.3. Choice of parent
If the branched monosaccharide forms a cyclic hemiacetal or hemiketal, the chain which includes the ring
atoms rather than any alternative open chain must be the basis of the name. Otherwise the parent is chosen
according to the principles given in 2-Carb-2.1.
Examples (see also Chart V):
CHO
I
HCOH
CHO
I
HCOH
I
I
HOC--CH
t
3
H3C--CH
I
HCOH
I
HCOH
HCOH
I
HCOH
I
CH2OH
I
CHzOH
3-C-Methyl-D-glucose
(configuration determined by OH)
3-Deoxy-3-methyI-D-glucose
(configuration determined by CH3)
CHO
I
CH2
I
O2N--?-CH3
MeOCH
I
HCOH
I
CH3
2,3,6-Trideoxy-3-C-methyl-4-O-methyl-3-nitro-D-lyxo-hexopyranose
(nitrogen has priority over carbon for determining configuration)
CHO
i
HCOH
I
C-CH2OH
~OH
I
CH2OH
4-Cyclohexyl-4-deoxy-4-(hydroxymethyl)-D-allose
[oxygen (in CH2OH) has priority over carbon (in cyclohexyl) at C-4]
or (4R)-4.cyclohexyl-4-deoxy-4-(hydroxymethyl)-o.ribo-hexose
If the two substituents at the branch point are identical, so that this centre has become achiral, the
stereochemistry is specified as described in 2-Carb-8.4.
Examples:
CliO
I
HCOH
I
CH3CCH
3
HCOH
I
HCOH
i
CH20H
3-Deoxy-3,3-dimethyI-D-ribo-hexose
CHO
I
HCOHI
HCOH
I
HOCH2--?-CHzOH
OH
4-C-(Hydroxymethyl)-D-erythro-pentose
Note. Cyclization of the second example between C-l and a CH2OH group would necessitate a three-centre configu
rational prefix for the ring form.
41
CH2OH
1
HOCH
1CHO
H
HOCH
.
. o.
H
#co. %
,I
t,,
I
I
. slc - - o X .,,OH
HOCH
H
HCOH
I
HCOH
HOCH2
I
CHO
1
2
ICHO
21
HCOH
7
CH2OH
61
H o c ~ O ~
5
H ~
t l
HOCH
1
OH' CH2OH
I
OH
I
HOCH
I
CHO
3
CHO
I
HO%iH H?OH
/
C--COH
OH3
C---H
I
c/ O.
CHO /
I
?H2
HCOH
I
CH3
5
HCOH
4
?,,HH
HC--C
OH
51
\ C ..~
HOCH
/ "'H
6L O CH2OH
71
CH20H
4
CHO
I
HCOH
I
HC--CH2--CH--CH2OH
I
H3C--CH
I
I
CH2OH
HOCH
I
CH2OH
6
1 3-Deoxy-3-[(lR,2S)-l,2-dihydroxy-3-oxopropyl]-D-glycero-D-altro-heptopyranose
or 3-deo×y-3-(D-threo- 1,2-dihydroxy-3-oxopropyl)-D-glycero-D-altro-heptopyranose
(not the alternative open-chain six-carbon dialdose or eight-carbon aldose, cf. 2)
2 4-Deoxy-4-(L-ribo-l,2,3,4-tetrahydro×ybutyl)-D-altro-hexodialdose
3 4-Deoxy-4-[(1R,2R)-l,2-dihydroxy-3-oxopropy[]-D-allo-heptulo-2,5-furanose
or 4-deoxy-4-(D-erythro- 1,2-dihydroxy-3-oxopropyl)-D-allo-heptulo-2,5-furanose
(not the alternative ketoaldose, cf. 4)
4 4-Deoxy-4-[(1R,2S)-l,2,3-trihydroxypropyl]-L-talo-heptos-6-ulose
or 4-deoxy-4-(L-erythro- l,2,3-trihydrnxypropyi)-L-talo-heptos-6-ulose
5 4,6-Dideoxy-3-C-(D-glycero-l-hydroxyethyl)-D-ribo-hexose
(not the alternative pentose)
6 3,4-Dideoxy-3-[3-hydroxy-2-(hydroxymethyl)propyl]-4-C-methyl-L-mannose
(not the alternative threo-hexose)
C h a r t V. Choice of parent in branched-chain monosaccharides. In the first names given for examples 1, 3
and 4, side-chain configuration is specified by use of R and S. This approach is generally preferred in all but
the simplest cases, as less open to misinterpretation.
Note. These recommendations may give rise to very different names for cyclic and acyclic forms of the same basic
structures, resulting from different priorities. Thus, in Chart V, structures 1 and 2 are virtually identical, differing only
by cyclization. The same holds for structures 3 and 4.
42
2-Carb-18.4. Naming the branches
Each branch will be named as an alkyl or substituted alkyl group replacing a hydrogen atom at the branch
point of the parent chain. Within the branches, configurations around asymmetric centres can either be
indicated using the R,S-system or, if they are carbohydrate-like and assignment is straightforward, by the use
of the configurational prefix. For this purpose, and in the absence of a carbonyl group (or a terminal COOH
or its equivalent) in the branch, the point of attachment of the branch (on the main chain) is regarded as
equivalent to an aldehyde group.
Example:
I
HOCH
i
HCOH
HOCH
i
HOCH
i
CH2OH
L-gluco-1,2,3,4,5-Pentahydroxypentyl
If there is a carbonyl group in the branch (or a terminal COOH or its equivalent), its position (assigned lowest
number when stereochemistry is being considered) is used to define the configurational prefix (see examples
1 and 3 in Chart V). Use of the R,S system is generally preferred, as less open to misinterpretation.
For an alternative approach to naming carbohydrate residues as substituents see 2-Carb-31.2 [which would
give the name ( 1R)- or (I S)-L-arabinitol- 1- C-yl for the above example, depending on the ligands at the branch
point].
2-Carb-18.5. Numbering
The carbon atoms of the parent chain are numbered according to 2-Carb-2.2.1. If a unique numbering is
required for the branch(es) (e.g. for X-ray or NMR work), the carbon atoms may be given the locant of the
appropriate branch point, with the internal branch locant as superscript, e.g. 4 2 for position 2 of the branch at
position 4 of the main chain. This style of branch numbering is not to be used for naming purposes: e.g. the
side-chain-methylated derivative of compound 5 is named 4,6-dideoxy-3-C-[(R)-1-methoxyethyl]-D-ribohexose, and not as a 31-O-methyl derivative.
2-Carb-18.6. Terminal substitution
See 2-Carb- 16.4.
2-Carb-19. Alditols
2-Carb-19.1. Naming
Alditols are named by changing the suffix '-ose' in the name of the corresponding aldose into '-itol'.
If the same alditol can be derived from either of two different aldoses, or from an aldose or a ketose, preference
is ruled by 2-Carb-2.1 or 2.2.2 as appropriate.
Examples:
CH2OH
CH2OH
HOCH
HCOH
HCOH
i
HOCH
HCOH
i
HOCH
HOCH
i
HCOH
HCOH
HCOH
HCOH
i
i
CH2OH
D-glycero-D-galacto-Heptitol
L-glycero-D-manno-heptitol
not
CH2OH
D-erythro-L-galacto-Octitol
D-threo-L-gulo-octitoI
not
43
CH2OH
I
CH2OH
I
HOCH
I
HCOH
I
HCOH
HCOH
I
HOCH
HCOH
t
HCOH
I
CH2OH
I
CH2OH
D-Arabinitol (Ara-ol) not D-lyxitol
D-Glucitol (GIc-ol) not L-gulitol
(the trivial name sorbitol is not recommended)
The trivial names fucitol and rhamnitol are allowed for the alditols corresponding to the 6-deoxy sugars fucose
and rhamnose.
CH2OHI
HOCH
I
HCOH
I
HCOH
I
HOCH
~ HzOH
HCOH
I
HCOH
I
HOCH
I
HOCH
I
CH3
I
CH 3
L-FucitoI (L-Fuc-oI) or 1-deoxy-D-galactitol
not 6-deoxy-L-galactitol (cf. 2-Carb-2.2.3.1)
L-Rhamnitol (L-Rha-ol) or 1-deoxy-L-mannitol
2-Carb-19.2. m e s o F o r m s
Alditols that are symmetric and therefore optically inactive - the m e s o forms - can be designated by the prefix
meso-.
Examples:
meso-Erythritol
meso-Ribitol
meso-Galactitol
The prefix D or L must be given when a derivative of a meso form has become asymmetric by substitution.
It is also necessary to define the configurational prefixes as D or L in the case where there are more than four
contiguous asymmetric carbon atoms.
Examples:
CH2OH
I
HCOHI
1
CH2OH
HOCH
I
HCOH
I
HOCH
I
HCOH
HCOH
I
HOCH
I
HOCH
I
HCOMe
I
CH2OH
I
7
meso-D-glycero-L-ido-Heptitol
not L-glycero-D-ido-heptitoI; cf. 2-Carb-2.2.3
CH2OH
5- O-Methyl-o-galactitol
not 2-O-methyI-L-galactitol
2-Carb-20. Aldonic acids
2-Carb-20.1. Naming
Aldonic acids are divided into aldotrionic acid, aldotetronic acids, aldopentonic acids, aldohexonic acids, etc.,
according to the number of carbon atoms in the chain. The names of individual compounds of this type are
formed by replacing the ending '-ose' of the systematic or trivial name of the aldose by '-onic acid'.
44
Examples:
COOH
I
HCOH
I
HOCH
I
HCOH
I
HCOH
I
CH2OH
COOI
HCOH
I
HOCH
I
HCOH
I
HCOH
I
CH2OH
D-Gluconic acid
COOH
I
HCNH2
I
HOCH
I
HCOH
I
HCOH
I
CHeOH
D-Gluconate
2-Amino-2-deoxy-D-gluconic acid
2-Carb-20.2. Derivatives
S a l t s are named by changing the ending '-onic acid' to '-onate', denoting the anion. If the counter ion is
known, it is given before the aldonate name.
Example:
Sodium D-gluconate
E s t e r s derived from the acid function are also named using the ending '-onate'. The name of the alkyl (aryl,
etc.) group is given before the aldonate name. Alternative periphrase names like 'aldonic acid alkyl (aryl, etc.)
ester' may be suitable for an index.
A m i d e s are designated by the ending '-onamide', and nitriles by the ending '-ononitrile'.
Examples:
/
COOMe
I
HCOH
I
HOCH
I
HCOH
I
HCOH
Me
COOCH
I
\
HCOH Me
I
HC-OMe
I
MeO-CH
I
HOCH
I
CONMe2
HOCH
I
HCOH
I
HOCH
I
CH2OH
CH2OH
Methyl D-gluconate
I
CH2OH
Isopropyl 3,4-di- O-methyI-L-mannonate
COOMe
I
HOCH
COOMe
I
HCOAc
I
CH 2
I
I
AcOCH
I
HCOH
AcOCH
I
I
CH2OH
Methyl
N,N-DimethyI-L-xylonamide
CH2OAc
3-deoxy-D-threo-pentonate
Methyl tetra- O-acetyI-L-arabinonate
L a c t o n e s are named with the ending '-onolactone'. The locants must be given (in the form '-ono-/,j-lactone):
that of the carbonyl group (i) is cited first, and that of the oxygen (j) second (see examples below). Periphrase
names (see alternatives in parentheses) appear widely in the literature but are not recommended. L a c t a m s are
named similarly by use of the ending '-onolactam'.
Examples:
CH2OH
HO(~.H~O-
CH2OH
~
CH2OH
°
H
OH
o-Glucono-1,4-1actone
(o-Gluconic acid T-lactone)
o-Glucono-1,5-1actone
([-Gluconic acid 8-1actone)
'~
oH -0
"c°"l
H(~O--.-.J
I
CHzOH
3-Deoxy-o-ribo-hexono-1,5-1actone
45
o
5-Amino-5-deoxy-D-mannono-1,5-1actam
Acyl halides are named by changing the ending '-onic acid' to '-onoyl halide'.
Example:
coct
I
HCOAc
z
AcOCH
I
HCOAc
I
HCOAc
I
CH2OAc
Penta-O-acetyI-D-gluconoyl chloride
More complicated examples of general principles for naming acid derivatives can be found elsewhere [ 13,14].
2-Carb-21. Ketoaldonic acids
2-Carb-21.1. Naming
Names of individual ketoaldonic acids are formed by replacing the ending'-ulose' of the corresponding ketose
by '-ulosonic acid', preceded by the locant of the ketonic carbonyl group. The anion takes the ending
'-ulosonate'. The numbering starts at the carboxy group.
In glycosides derived from ketoaldonic acids, the ending is '-ulosidonic acid', with appropriate ring-size infix,
e.g. '-ulopyranosidonic acid'.
Examples:
COOH
I
HOCH
COOH
I
I
C=O
I
HCOH
I
HCOH
HCOH
I
HCOH
I
C=O
I
I
CH2OH
CH2OH
D-erythro-Pent-2-ulosonic acid
D-arabino-Hex-5-ulosonicacid
H
HH ~ O
.
COOH
o, ,o H
HO
H
{~
HOOC--?OH
1
.oc.
/
H20H
HOCH
OH ~ O ~ c
.
CH20
H
.co.,
.co
oo.
H
(~-D-arabino-Hex-2-ulopyranosonicacid
3-Deoxy-et-D-manno-oct-2-ulopyranosonicacid
Note. The last of the above examples is one of the possible forms of the compound referred to by the three-letter symbol
Kdo (formerly the abbreviation KDO, from the previously allowed trivial name ketodeoxyoctonic acid). Similarly the
symbol Kdn for the C9 sugar 3-deoxy-D-glycero-D-galacto-non-2-ulopyranosonic acid is widely used.
2-Carb-21.2. Derivatives
Esters, lactones, lactams, acyl halides etc. are named by modifying the ending '-ic acid' as described for
aldonic acids (2-Carb-20.2).
46
Examples:
H
E,ooc foMe/
ooE,
I\,H
.o~
(o~e
HO/I
HO
.o?.
/
~co~jI
-=
HCOH
H
CH20
Ethyl (methyl ct-D-arabino-hex-2-ulopyranosid)onate
Note.
The parentheses are inserted to distinguish between the ester alkyl group (cited first) and the glycosidic O-alkyl
group.
H
0
0J,
l
.o,°
H
0
.oc-c
.oc.,
C:O
I
OCH2
p-D-arabino-Hex-2-ulopyranosono-1,5-1actone
~H2OH
H
Indol-3-yl D-xylo-hex-5-ulofuranosonate;
trivial name isatan B
(~H2OH
CH2OH
I
i~
H
0
0
~
v
HO
L-xylo-Hex-2-ulosono-l,4-1actone
~
0
OH
OH'
L-threo-Hex-2-enono-l,4-1actone
"(3
L-/yxo-Hex-2-ulosono-l,4-1actone
(L-Ascorbic acid is the equilibrium mixture of all three isomers)
2-Carb-22. Uronic acids
2-Carb-22.1. Naming and numbering
The names of the individual compounds of this type are formed by replacing (a) the '-ose' of the systematic
or trivial name of the aldose by '-uronic acid', (b) the '-oside' of the name of the glycoside by '-osiduronic
acid' or (c) the '-osyl' of the name of the glycosyl group by '-osyluronic acid'. The carbon atom of the
(potential) aldehydic carbonyl group (not that of the carboxy group as in normal systematic nomenclature
[13,14]) is numbered 1 (see 2-Carb-2.1, note 1).
2-Carb-22.2. Derivatives
Derivatives of these acids formed by change in the carboxy group (salts, esters, lactones, acyl halides, amides,
nitriles, etc.) are named according to 2-Carb-20.2. The anion takes the ending '-uronate'. Esters are also named
using the ending '-uronate'.
Examples:
CHO
I
HCOH
I
HOCH
I
HCOH
I
HCOH
I
COOH
D-Glucuronic acid
.o~\
HO " ~ " " ~
OH
o~-D-Mannopyranuronic acid
4"/
H
HO --
COOH O
H'-O~O
Ph
Pheny113-D-glucopyranosiduronicacid
notpheny113-D-glucuronosideor phenylglucuronide
COOMe ,-~
HOI~ ~/HI
I
I
H OH
Methyl (X-L-idopyranosiduronicacid
AcO~ , , , , , , , , , , " " ~
AcO
I
Br
Methyl 2,3,4-tri-O-acetyl-(~-D-glucopyranosyluronate bromide
H~O~?Me
F,3
H
OH
I
H
OH
H
COONa
CN
Sodium (methyl a-L-glucofuranosid)uronate
Methyl ~-L-glucofuranosidu rononitrile
f'~
HCOH
H
BzOCH
i
=BzOCH
I
OH
HCOl
HCOBz
I
COOEt
Ethyl 2,3,5-tri-O-benzoyl-c~-D-mannofu ranuronate
CHO
I
HCOH
I
O--CH
HICOH
I HCOH
t___ c--O
~
COOEt
I
BzOC~IoB O ~
zB
H ~
H
H
O--C
I
Me
F',,Y ."71>1
.oc., "l---r "
"71>1
HOCH~
I
y / O ~ ?
D-Glucurono-6,3-1actone
O=C
IH
HOC
I ~/ o ~H
o
H, OH
H
H ~
H
OH
OMe
OH
Methyl c(-o-glucofuranosidu rono-6,3-1actone
D-Glucofuranu rono-6,3-1actone
COOMe
COOH
H, OH
H, OH
H
H
OH
OH
Methyl 4-deoxy-L-threo-hex-4-enopyranuronate
4-Deoxy-L-threo-hex-4-enopyranuronicacid
COOH
O H ~ I
H
Methyl
Me
OH
4-deoxy-~-k-threo-hex-4-enopyranosiduronicacid
48
COOMe
Ph
H
ON
Methyl (phenyl 4-deexy-[~-L-throo-hex-4-enopyranosid)uronate
HO
I CONH2
H
O
~
OMe
OH
Methyl J]-D-galactopyranosiduronamide
2-Carb-23. Aldaric acids
2-Carb-23.1. Naming
Names of individual aldaric acids are formed by replacing the ending '-ose' of the systematic or trivial name
of the parent aldose by '-aric acid'. Choice between possible names is based on 2-Carb-2.2.2.
Examples:
COOH
COOH
I
COOH
COOH
HCOH
HCOH
I
I
HOCH
HOCH
I
HOCH
HOCH
I
HCOH
HOCH
HCOH
I
I
COOH
COOH
L-Altradc acid
not L-talanc acid
D-Glucaric acid
not L-gularic acid
I
~
I
HOCH
I
HCOH
HOCH
I
I
I
HCOH
HCOH
I
HCOH
HCOH
I
I
HOCH
HOCH
I
I
COOH
COOH
L-glycer~D-ga~ct~Heptaric
acid
not L-glycer~D-g~c~heptaricacid
2-Carb-23.2. meso Forms
To the names of aldaric acids that are symmetrical, which therefore have no D- or L- prefix, the prefix 'meso-'
may be added for the sake of clarity. Examples: meso-erythraric acid, meso-ribaric acid, meso-xylaric acid,
meso-allaric acid, meso-galactaric acid.
The D or L prefix must however be used when a meso-aldaric acid has become asymmetric as a result of
substitution.
Examples:
COOH
COOH
COOH
I
I
HCOH
I
HCOH
HOCH
HOCH
HOCH
MeO-CH
I
HCOH
I
I
HCOH
I
I
HOCH
I
I
I
HCOH
HCOH
I
I
COOH
COOH
mes~Xylaricacid
mes~Galactaricacid
I
COOH
4- O-MethyI-D-galactaric acid
not 3-O-methyI-L-galactadc acid
2-Carb-23.3. Trivial names
For the tetraric acids, the trivial name tartaric acid remains in use, with the stereochemistry given using the
R,S system. Esters are referred to as 'tartrates' (the second 'a' is elided).
Examples:
COOH
I
HCOH
I
HOCH
I
COOH
COOH
I
HOCH
I
HCOH
I
COOH
COOH
I
HCOH
I
HCOH
I
COOH
(2R,3R)- or (+)-Tartaric acid
(2S,3~- or (-)-Tartaric acid
(2R,3~- or meso-Tartaric acid
or L-threaric acid
or D-threaric acid
or erythraric acid
49
Note. In the older literature, there is confusion about the use of D and L in the case of tartaric acids. It is therefore
recommended to use the R,S system in this case.
2-Carb-23.4. Derivatives
Derivatives formed by modifying the carboxy group (salts, esters, lactones, lactams, acyl halides, amides,
nitriles etc.) are named by the methods of 2-Carb-20.2. Dilactones, half-esters, amic acids etc. are named by
the methods of [13, 14]. In cases of ambiguity, locants should be specified.
Examples:
COOMe
I
HCOH
I
HOCH
I
HOCH
I
HCOH
I
COOH
COOH
I
HCOH
I
HOCH
I
HOCH
I
HCOH
I
COOMe
1-Methyl hydrogen D-galactamte
CONH2
I
HCOH
I
HOCH
I
HCOH
I
HCOH
I
COOH
6-Methyl hydrogen D-gala~arate
COOMe
HCOH
D-Gluca~l-amic acid
O
OH
I
HOCH
HCOH
I
HCOH
I
CONH2
H.......... H
HO
O
L-Mannaro-1,4:6,3-dilactone
Methyl D-gluca~6-amate
2-Carb-2~ O-Subs~tu~on
2-Carb-24.1. Acyl (alkyl) names
Substituents replacing the hydrogen atom of an alcoholic hydroxy group of a saccharide or saccharide
derivative are denoted as O-substituents. The 'O-' Iocant is not repeated for multiple replacements by the
same atom or group. Number locants are used as necessary to specify the positions of substituents; they are
not required for compounds fully substituted by identical groups. Alternative periphrase names for esters,
ethers, etc. may be useful for indexing purposes. For cyclic acetals see 2-Carb-28.
Examples:
HC=O
i
HCOAc
I
AcOCH
I
HCOAc
I
HCOAc
I
CH2OAc
Penta-O-acetyl-alOohydo-D-glucose
2,4-Di-O-acetyl-6-O-trityI-D-glucopyranose
or a/dehydo-D-glucose pentaacetate
CH2OBz
HO
I CH2OM~)
HO~~oUH
BzO-JI~"~'~
BzO Br
OH
6-O-MethanesulfonyI-D-galactopyranose
or D-galactopyranose 6-methanesulfonate
Tetra-O-benzoyl-cc-D-glucopyranosyl bromide
MeO
I CH2OM~)
°
OH
4,6-Di-O-methyl-~-D-galactopyranose
50
Note. Acyl substituents on anomeric OH are designated (as above) by O-acyl prefixes. However, anomeric O-alkyl
derivatives are named as glycosides (see 2-Carb-33).
2-Carb-24.2. P h o s p h o r u s oxoacid esters
24.2.1.
Phosphates
Of special biochemical importance are the esters of monosaccharides with phosphoric acid. They are generally
termed phosphates (e.g. glucose 6-phosphate). In biochemical use, the term 'phosphate' indicates the
phosphate residue regardless of the state of ionization or the counter ions.
The prefix terms used for phosphate esters in organic nomenclature ([14], p.65) are 'O-phosphono-' and
'O-phosphonato-' for the groups (HO)2P(O)- and (O-)2P(O)- respectively, bonded to oxygen.
The term 'phospho-' is used for (HO)2P(O)- or ionized forms in a biochemical context (see recommendations
for the nomenclature of phosphorus-containing compounds [24]).
If a sugar is esterified with two or more phosphate groups, the compound is termed bisphosphate, trisphosphate
etc. (e.g. fructofuranose 1,6-bisphosphate). The term diphosphate denotes an ester with diphosphoric acid,
e.g. adenosine 5'-diphosphate.
Note. In abbreviations, a capital P is used to indicate a terminal -PO3H2 group or a non-terminal -PO2H- group (or
dehydronated forms).
Examples:
H°OH
OHoPo32-
HO
D-Glucopyranose 6-(dihydrogen phosphate)
or 6-O-phosphono-D-glucopyranose
~-D-Glucopyranosyl phosphate
(biochemical usage: glucose 1-phosphate) (Glcl P)
OPO32-
HCoH
I
H ~ - ~
OH
CH2OPO32- OH
H
D-Fructofuranose 1,6-bisphosphate
(often shortened to fructose 1,6-bisphosphate)
or 1,6-di-O-phosphonato-D-fructofuranose
or 1,6-bisphospho-D-fructofuranose
D-Glucopyranose 6-phosphate
(often shortened to glucose 6-phosphate)
or 6- O-phosphonato-D-glucopyranose
or 6-phospho-D-glucose (GIc6P)
(in a biochemical context)
COOH
O~\0OPO32I
HCOH
I
H2COPO32-
OPO3Hz
3- O-Phosphonato-D-glyceroyl phosphate
or 3-phospho-D-glyceroyl phosphate
or 1,3-bisphospho-D-glycerate (for biochemical usage)
~-D-Glucopyranuronic acid
1-(dihydrogen phosphate)
(biochemical usage: glucuronate 1-phosphate) (GIcA1P)
N~J~.N~ j
0
Il
O-
o-
o
I
I
I
5'
-O--P--O--P--O--CH2
I
LI
I Y
O
~
I
I
H T------[ H
HO OH
Adenosine 5"-diphosphate (ADP) or 5'-diphosphoadenosine
51
6"
0
CH2OH
I,
"-
H
H
OH
-O-~H2 o°
i<~. H'~.~,"
~'P'--K'"
:°-_
I
I
HO
OH
Uridine 5'-(c~-D-glucopyranosyl diphosphate)
(trivial name uridinediphosphoglucose) (UDP-GIc)
NH2
.t
OH
I
O--P--O--CH2
i .5..~O~'N
I
o.¢ COOH
HOCH2
.
O-
H
A c N H ~ ~ , ~
HO
O
H
HO
j
OI H H
Cytidine 5"-(5-acetamido-3,5-dideoxy-D-glycero-~-D-galacto-non-2-ulopyranosylonic acid
monophosphate) (CMP-~-Neu5Ac)
24.2.2. Phosphonates
The following examples illustrate the use of phosphonate terminology for esters of phosphonic acid,
HP(O)(OH)2. For formation of the alternative (substitutive) names, see 2-Carb-31.2.
Examples:
o
II
HO-P--OCH 2 j O . ~
HO
OMe
OH
Methyl 13-D-dbofuranoside5-(hydrogen phosphonate)
or methyl 5-deoxy-~-D-ribofuranosid-5-ylhydrogen phosphonate
O
~CH3
OH
COOMe
!
/
H~"
o
,o o
oH
I~
--~.~...~
7
~'~H
Na
H
a'-Azido-3'-deox3/thymi6ine 5'-[(methyl 5-acetamido-3,5-dideow-D-glycero-e~-D-galactonon-2-ulopyranosylonate) phosphonatel
Derivatives substituted on phosphorus are named by standard procedures [ 13, 14]; e.g. P-methyl derivatives
are named as methylphosphonates.
Compounds with a phosphonate group linked by a P - C bond to a carbohydrate residue may be named as
glycos-n-ylphosphonates (cf. 2-Carb-31.2) or as C-substituted carbohydrates (cf. amino sugars, 2-Carb-14).
Example:
CH2OH
H O ~ o
H
OP(OMe)2
2-Deoxy-2-dimethoxyphosphoryI-D-glucopyranose
(this usage of 'phosphoryr is given in [13], Section D, Rule 5.68, and [14], p. 65)
or dimethyl 2-deoxy-D-glucopyranos-2-ylphosphonate
52
24.2.3. Phosphinates
Esters of phosphinic acid, H2P(O)(OH), are named by the same methods as used for phosphonates. For
examples with two P - C bonds see 2-Carb-31.3.
2-Carb-24.3. Sulfates
The prefix terms used for sulfuric esters are 'O-sulfo-' and 'O-sulfonato-', for the groups (HO)S(O)2- and
(O-)S(O)2- respectively, bonded to oxygen. Sulfates may also be named by citing the word 'sulfate', preceded
by the appropriate locant, after the carbohydrate name.
Example:
HO
HON~--~~O
H
SO3-
Oc-D-Galactopyranose2-sulfate
or 2-O-sulfonato-a-D-galactopyranose
The mixed sulfuric phosphoric anhydride (PAdoPS or PAPS) of 3"-phospho-5'-adenylic acid is named as an
acyl sulfate:
O
O
N
N
ii
II
(" I ' @ ~
O~-S--O--P--O--CH2 jO__ ~ - , ' ~ . )
H
H
o ~ ~1oo. ~
O:'~P--O
I
O-
3'-Phospho-5'-adenylyl sulfate (PAPS)
2-Carb-25. N-Substitution
Substitution, e.g. acylation, at the NH2 group of an amino sugar can be dealt with in two different ways:
(a) The whole substituted amino group can be designated as a prefix, e.g. 2-acetamido- (or 2butylamino-) 2-deoxy-D-glucose. For the purpose of the configurational prefix, the group is considered
to take the place of the former OH group.
(b) If the amino sugar has a trivial name, the substitution is indicated by a prefix preceded by an italic
capital N.
Note. In carbohydrate nomenclature, substitution at a heteroatom is normally indicated by citing the locant of the
attached carbon atom, followed by a hyphen, and then the italicized heteroatom element symbol, e.g. 2-O-methyl,
5-N-acetyl. Substituents on the same kind of heteroatom are grouped (e.g. 2,3,4-tri-O-methyl), and substituents of the
same kind are cited in alphabetical order of heteroatoms (e.g. 5-N-acetyl-4,8,9-tri-O-acetyl).The alternative format with
superscript numerical locants (e.g. N 5 ,O 4 ,O 8,O 9-tetraacetyl), used in some other areas of natural product chemistry, is
unusual in carbohydrate names.
Examples:
CH2OAc
I
HCN(Me)Ac
I
AcOCH
I
HCOAc
l
HCOAc
I
CH2OAc
1,3,4,5,6-Penta-O-acetyl-2-deoxy-2-(N-methylacetamido)-D-glucitol
53
OH
HO
H,,, ,,,,OH
H
AcOCH2_~',,C~OAc
COOH
(~OOH
.o.,,o,.-7---o117-o.
HOCH2 -- ICI--H N ~ _ _ _ , ~ , ~ ' ~
O
N H "OH
SO3H
2-Deoxy-2-sulfoamino-D-glucopyranose
or N-sulfo-D-glucosamine
OH
2-Acetamido-2-deoxy-D-galactopyranose
or N-acetyI-D-galactosamine
AO" N ~ _ _ _ , ~ " ~ l ~
OH
AcO
5-N-Acetyl-4,8,9-tri-O-acetyl-eL-neuraminicacid
N-Glycoloyl-c~-neuraminic acid (c~-Neu5Gc)
(O is implied in the trivial name)
(cc-Neu4,5,8,9Ac4)
2-Carb.26. lntramolecular anhydrides
An intramolecular ether (commonly called an intramolecular anhydride), formally arising by elimination of
water from two hydroxy groups of a single molecule of a monosaccharide (aldose or ketose) or monosaccharide derivative, is named by attaching the (detachable) prefix 'anhydro-' preceded by a pair of locants
identifying the two hydroxy groups involved.
Note. Detachable prefixes are cited in alphabetical order along with any substituent prefixes.
Examples:
MeO
MeO
I
I
CHO
HO
3,6-Anhydro-2,4,5-tri-O-methyI-D-glucose
I
OH
H
2,5-Anhydro-D-allononitrile
CH2OH 0
MeOC~-@"O I H ~ O M e
H
OH
H
1,5-Anhydro-D-galactitol
OMe
Methyl 3,6-anhydro-2,5-di-O-methyl-13-D-glucofuranoside
AoN.A
V"H?OH
o"
CO2H
CH2OH
OH
5-Acetamido-2,6-anhydro-3,5-dideoxy-D-glycero-D-galacto-non-2-enonic acid (Neu2en5Ac)
The compounds usually known as monosaccharide anhydrides or glycose anhydrides (earlier 'glycosans'),
formation of which involves the anomeric hydroxy group, are named by the same procedure. In these cases
the order of preference of ring size designators is pyranose > furanose > septanose. However, three- or
four-membered rings should normally be cited as 'anhydro' if there is a choice.
Trivial names for anhydro monosaccharides, though established by usage, are not recommended because of
possible confusion with polysaccharide names based on the use of the termination '-an'.
54
Examples:
~
OH
OH
0
CH2OH
OH
2,7-Anhydro-[3-D-altro-hept-2-ulopyranose
1,6-Anhyd ro-~-D-glucopyranose
not 1,5-anhydro-ct-D-glucoseptanose
(older trivial name: levoglucosan)
(older trivial name: sedoheptulosan)
CH2OAc
AcO~ ' - - - - - ~ O.
O
O
A~O&
o
3,4,6-Tri-O-acetyl-1,2-anhydro-cc-D-glucopyranose
not 3,4,6-td-O-acetyI-1,5-anhydro-~-D-glucooxirose
I
OH
1,6:3,4-Dianhydro-~-D-talopyranose
O
1,6-Anhydro-3,4-dideoxy-~-D-glycero-hex-3-enopyranos-2-ulose
(trivial name: levoglucosenone)
1,4-Anhydro-~-D-galactopyranose
2-Carb-27. Intermolecular anhydrides
The cyclic product of condensation of two monosaccharide molecules with the elimination of two molecules
of water (commonly called an intermolecular anhydride), is named by placing the word 'dianhydride' after
the names of the two parent monosaccharides. When the two parent monosaccharides are different, the one
preferred according to the order of preference given in 2-Carb-2.1 is cited first. The position of each anhydride
link is indicated by a pair of locants showing the positions of the two hydroxy groups involved; the locants
relating to one monosaccharide (in a mixed dianhydride, the second monosaccharide named) are primed. Both
pairs of locants immediately precede the word 'dianhydride'.
Examples:
H
I\
H
OH
H
HO/\
,o
OH
H
H
c~-o-Fructopyranose ~-D-fructopyranose 1,2':l',2-dianhydride
H
H
o
HO
H
H
OH
Ct-D-Fructopyranose t~-D-sorbopyranose 1,2":l',2-dianhydride
H
H
OH
HO
(,~-D-Galactopyranuronic acid) 13-L-rhamnopyranose 1,2':l',2-dianhydride
2-Carb-28. Cyclic acetals
Cyclic acetals formed by the reaction of saccharides or saccharide derivatives with aldehydes or ketones are
named in accordance with 2-Carb-24.1, bivalent substituent names (formed by general organic nomenclature
principles) being used as prefixes. In indicating more than one cyclic acetal grouping of the same kind, the
appropriate pairs of locants are separated typographically when the exact placement of the acetal groups is
known.
Examples:
CH2OH
HOCH2
H?o\
I
I
HO?H/CH2
HCO
I
CH2OH
1%oH ;
HO
CH2OH
H ~
H
2,4- O-Methylenexylitol
..
Ot
O--CMe2
1,2-O-Isopropylidene-(z-D-glucofuranose
Me2C.~OCH2
OCH
I
HOCH
I
HCOH
I
HCO----.
^.
I /L;Me2
OMe
H2CO
1,2:5,6-Di-O-isopropylidene-D-mannitol
Methyl (R)-4,6-0-benzylidene-c(-D-glucopyranoside
p h " ~ 0~'~
O--...C
[""H
° Me
Ph
Methyl (S)-2,3:(R)-4,6-di-0-benzylidene-(z-o-allopyranoside
B ~
CH2OBz
C!....~OMe
3,4,6-Tri-O-benzoyl-[(S)-1,2-O-chloro(methoxy)methylene]-I~-D-mannopyranose
cO o\
AcOV
~ IO
MeO,,,,,,~"O
OH3
3,4,6-Tri-O-acetyl-et-D-glucopyranose (R)-1,2-(methyl orthoacetate)
or 3,4,6-tri-O-acetyl-[(Fi')-1,2-O-(1-methoxyethylidene)]-(z-g-glucopyranose
Note 1. The last two examples contain cyclic ortho ester structures. These compounds are conveniently named as cyclic
acetals.
Note 2. In the last four examples, new asymmetric centres have been introduced at the carbonyl carbon atom of the
aldehyde or ketone that has reacted with the saccharide. When known, the stereochemistry at such a new centre is
indicated by use of the appropriate R or S symbol ([ 13], Section E) placed in parentheses, immediately before the locants
of the relevant prefix.
56
2-Carb-29. Hemiacetals, hemiketals and their thio analogues
The compounds obtained by transforming the carbonyl group of the acyclic form ofa saccharide, or saccharide
derivative, into the grouping:
\
/OR
\
/C\o H
,
..OR
\
/C\s H
,
/SR
\
/C\o H
or
/SR
/C\s H
(R = alkyl or aryl)
are named as indicated in 2-Carb-30, by using the terms 'hemiacetal', 'monothiohemiacetal', or 'dithiohemiacetal' (or the corresponding 'hemiketal' terms for ketone derivatives), as appropriate. The two isomers
of a monothiohemiacetal are differentiated by use of O and S prefixes.
Examples:
OEt
I
HCOH
i
HCOBz
i
BzOCH
I
HCOBz
I
HCOBz
i
CH2OBz
SEt
I
HCSH
I
HCOBz
I
BzOCH
I
HCOBz
I
HCOBz
I
CH2OBz
(1S)-2,3,4,5,6-Penta- O-benzoyI-D-glucose
ethyl dithiohemiacetal
(1 ,S)-2,3,4,5,6-Penta-O-benzoyI-D-glucose
ethyl hemiacetal
OEt
i
HCSH
i
HCOBz
i
BzOCH
i
HCOBz
i
HCOBz
i
CH2OBz
SEt
i
HCOH
i
HCOBz
i
BzOCH
i
HCOBz
i
HCOBz
i
CH2OBz
(1 R)-2,3,4,5,6-Penta-O-benzoyI-D-glucose
O-ethyl monothiohemiacetal
(1 S)-2,3,4,5,6-Penta-O-benzoyI-D-glucose
S-ethyl monothiohemiacetal
Note. In these compounds carbon atom number 1 has become chiral. When known, the stereochemistry at this new
chiral centre is indicated using the R,S system ([13], Section E).
2-Carb-30. Acetals, ketals and their thio analogues
The compounds obtained by transforming the carbonyl group of a saccharide or saccharide derivative into
the grouping:
\
/OR 1
\
/C\oR2
/OR 1
/C\sR2
\
or
/ SR~
/C\sR2
(R = alkyl or aryl)
are named by placing after the name of the saccharide or saccharide derivative the term 'acetal',
'monothioacetal' or 'dithioacetal' (or the corresponding 'ketal' terms for ketone derivatives) as appropriate,
preceded by the names of the groups R 1 and R 2. With monothioacetals, the mode of bonding of two different
groups R 1 and R 2 is indicated by the use of the prefixes O and S.
Examples:
HO(OEt)2
HCOH
I
HOCH
I
HCOH
I
HCOH
I
CH2OH
D-Glucose diethyl acetal
?H2OH
?(OEt)2
HOCH
I
HCOH
I
HCOH
I
CH2OH
D-Fructose diethyl ketal
/S-CH2~
HC\
.CH2
IS_OH/
HCOH
I
HOCH
I
HCOH
I
HCOH
I
CH2OH
D-Glucose propane-1,3-diyl dithioacetal
57
SEt
i
HCOMe
i
HCOH
I
HOCH
t
HCOH
i
HCOH
i
CH2OH
OMe
i
HCSMe
i
HCOAc
I
AcOCH
I
HCOAc
I
HCOAc
i
CH2OAc
(1 S)-D-Glucose S-ethyl
O-methyl monothioacetal
(1 R)-2,3,4,5,6-Penta-O-acetyI-D-glucose
dimethyl monothioacetal
Note. In the last two examples, carbon atom 1 has become chiral. When known, the stereochemistry at this new chiral
centre is indicated by the R,S system, as specified in 2-Carb-29.
2-Carb-31. Names for monosaccharide residues
2-Carb-31.1. Glycosyl residues
The residue formed by detaching the anomeric hydroxy group from a monosaccharide is named by replacing
the terminal '-e' of the monosaccharide name by '-yl'. The general name is 'glycosyl' residue. Terms of this
type are widely used in naming glycosides and oligosaccharides. For examples (including glycosyl residues
from uronic acids), see 2-Carb-33.2. The term 'glycosyl' is also used in radicofunctional names, e.g. for
halides such as the glucopyranosyl bromide in 2-Carb-24. I and the mannopyranosyl fluoride in 2-Carb- 16.1,
and esters such as the glucopyranosyl phosphate in 2-Carb-24.2.1 and the mannopyranosyl nitrate in
2-Carb- 16.2.
2-Carb-31.2 Monosaccharides as substituent groups
In order to produce names for structures in which it may be desirable for a non-carbohydrate portion to be
cited as parent, prefix terms are required for carbohydrate residues linked through carbon or oxygen at any
position on the main chain. These prefixes can be formed by replacing the final 'e' of the systematic or trivial
name of a monosaccharide by '-n-C-yl', '-n-O-yl' or '-n-yl' (if there is no ambiguity). In each case the term
'-yl' signifies loss of H from position n. At a secondary position (e.g. in 2-deoxy-D-glucos-2-yl, below) the
free valency is regarded as equivalent to OH for assignment of configuration.
Examples:
CH2_
I
C=O
1
HOCH
I
HCOH
I
HCOH
I
CH2OH
1-Deoxy-o-fructos-1 -yl
CHO
I
--COH
I
HOCH
I
HCOH
CHO
1
--CNH2
I
HOCH
I
HCOH
I
HCOH
I
CH2OH
.o-k---._J\
~
OH
2-Amino-2-deoxy-D-glucos-2-yl
CHO
I
I
HOCH
I
HCOH
I
I
HCOH
CH2OH
D-Glucos-2-C-yl
(Methyl 13-D-ribopyranosid-2- O-yl)
HC--
HCOH
I
OMe
I
CH2OH
2-Deoxy-o-glucos-2-yl
]'he same endings can be used to form substituent prefixes for alditol residues.
58
Examples:
?H2OH
HOCH
I
--CH
I
HCOH
I
HCOH
I
CH2OH
I
CHOH
I
HCOH
I
HOCH
I
HOCH
I
CH2OH
3-Deoxy-D-mannitol-3-yl
L-Arabinitol-1-C-yl (cf. 2-Carb-18.4)
(R/S to be specified at C-1)
The ending '-yl' without locants signifies loss of OH from the anomeric position (see 2-Carb-3 I. l). Loss of
H from the anomeric OH is indicated by the ending '-yloxy', without locant. For examples see 2-Carb-33.
The situation in which the anomeric OH is retained but H is lost from the anomeric carbon atom is indicated
by use of the ending '-yl' without locants in conjunction with the prefix 'l-hydroxy-' (not by the ending
'-l-C-yl'). N.B. In this case, the anomeric prefix t~ or 13refers to the free valency, not the OH group.
Example:
H
O
~
OH
HO
1-Hydroxy-c(-D-allopyranosyl
Examples
of the u s e of substituent prefixes for c a r b o h y d r a t e
residues:
A C O ~ O A c
AcO
HO" f ~ ' ~ O ~
~ / ~ ' ~
[~
.6
+
/CH3
OH2--NH2--C~,,H
~"
OH
COO-
COCI
4-(1-Acetoxy-2,3,4,6-tetra-O-acetyl-c(-D-allopyranosyl)benzoylchloride N-(1-Deoxy-D-fructopyranos-1-yl)-L-alanine
HO
HO
CH2 N
CH3
N,N-Bis-(1 -deoxy-D-fructopyranos-l-yl)-p-toluidine
coo
c.,
\
Is
"
N ~I~N/.G "1
",.,>1
H
HO OH
H T---r
S-(5"-Deoxyadenosin-5"-yl)-L-methionine (AdoMet)
S-[(1-Adenin-9-yl)-1,5-dideoxy-13-D-ribofuranos-5-yl]-L-methionine
[trivial name S-adenosylmethionine(SAM)]
59
p,o Z,o
CH2--S
O
OH
S--H2C
OH
O
OH
OH
OH
OH
Bis(5-deoxy-13-D-ribofuranos-5-yl) disulfide
or bis(5-deoxy-13-D-ribofuranos-5-yl)disulfane
CH2OH,.-,
O~CHzCOOH
(13-g-Glucopyranos-2-O-yl)acetic acid
(more commonly named 2-O-carboxymethyl-I~-D-glucopyranose; see 2-Carb-2.1, note 2)
CH2OH
HOOC--CO-CH2--OH O ~ ~
HO I
OMe
(Methyl ~-D-glucopyranosid-4-O-yl)pyruvic acid [or methyl 4-O-(oxalomethyl)-~-D-glucopyranoside]
CH2OH,..,
HOf k ~ ' ~ ' ~
o
H
3-(13-D-Glucopyranosyloxy)indole (or indol-3-y113-D-glucopyranoside); trivial name indican
HO
HOCH2~OH
HO OMe
~,,,,,,,~f3~,,,...~.CH20H
OMe
X=O
Methyl 2-O-(methyl 2-deoxy-~-D-glucopyranosid-2-yl)-c~-D-glucopyranoside
or bis(methyl 2-deoxy-c~-D-glucopyranosid-2-yl) ether
X=NH
Bis(methyl 2-deoxy-(z-D-glucopyranosid-2-yl)amine
2-Carb-31.3. Bivalent and tervalent groups
The group formed by detaching one hydrogen atom from each of two (or three) carbon atoms of a
monosaccharide is named by replacing the terminal '-e' of the monosaccharide name by '-diyl' (or '-triyl'),
preceded by the appropriate locants.
Examples:
/
OH
T~
MeO/
CH2OH
/..OH
OH
Methyl 13-D-talopyranose-2-C,4-C-diylphosphinite
or 2-C,4-C-(methoxyphosphanediyl)-13-o-glucopyranose
or (2R,4 S)-2-C,4-C-(methoxyphosphanediyl)-~-o-threo-hexopyranose
60
/ OH
CH2OH
/
MeO
Methyl (ethyl 2,4-dideex31-~-D-glucopyraneside-2,4-diyl)phosphinite
or ethyl 2,4°dideew-2,4-(methexyphesphanediyl)-~-D-glucopyraneside
Residues formed by detaching two (or three) hydrogen atoms from the same carbon atom may be named
similarly.
Example:
HC=PPh 3
He ~ . ~
H
H
OH
5
(Methyl 6-deoxy-l~-o-glucopyranosid-6-ylidene)triphenyI-X-phosphane
or methyl 6-deoxy-6-triphenyl-Z,5-phosphanylidene-I~-D-glucopyranoside
Note. Names based on phosphane, rather than phosphine or phosphorane, are used in this document, as recommended
in [14].
2-Carb-32. Radicals, cations and anions
Naming procedures described in this section follow the recommendations given in [25].
2-Carb-32.1. Radicals
Names for.radicals are formed in the same way as those for the corresponding substituent groups (see
2-Carb-31.2).
Examples:
CH2OMe
f
C--O
CH2OBn
BnO
B n O ~
BnO
MeOC.
I
HCO'I
HCOMe
I
CH2OMe
~H
Tetra-O-benzyI-D-glucopyranosyl
1,3,5,6-Tetra-O-methyI-D-fructos-4-O-yl
CHzOBn
BnO-X--_\
BnO~oMe
2,3,4,6-Tetra-O-benzyl-l-methoxy-D-glucopyranosyl
Carbenes are named analogously by use of the suffix '-ylidene'.
Example:
7
-°
OH
Methyl 2-deoxy-I~-D-erythro-pentopyranosid-2-ylidene
61
2-Carb-32.2. Cations
Cations produced by formal loss of H- from a carbon atom are denoted by replacing terminal 'e' with the
suffix '-ylium', in conjunction with appropriate locants and a 'deoxy-' prefix if necessary (cf. 2-Carb-31.2).
Examples:
CH2OH
HO\o~'
HOCH
' OHO
I
HCOH
,
HCOH
I
CH2OH
D-arabino-Hexos-2-C-ylium
HOOH
H\o+/,OHO
H~ H
I
HCOH
,
HCOH
I
CH2OH
CH2OH+
O
H~+ H
H~OH
H
H
HO ~....~
H
2-Deoxy-D-arabino-hexos-2-ylium
HO ~ i l
OH
H
O
HN,~".
H
/ "
OH
D-Glucopyranosylium
CH2OAc
A
c
O
~
Io
Aco
C+
/
CH3
3,4,6-Tri-O-acetyl-1,2- O-ethyliumdiyl-a-D-allopyranose
Cations formed by hydronation of an OH group or at the hemiacetal ring oxygen are denoted by the suffix
'-O-ium', with numerical locant.
Examples:
MeO.~_~............~O
~ O M e
I
~"OH2
OMe
Methyl 3,4-dioO-methyl-13-o-dbopyranosid-2-O-ium
H
O÷
MeO~____------~OMe
i
OMe
OMe
Methyl 2,3,4-tri-O-methyl-13-D-ribopyranosid-5-O-ium
2-Carb-32.3. Anions
Anions produced by formal loss of H + from an OH group are denoted by the suffix '-O-ate', with numerical
locant.
Example:
MeO~-"""-"~ O~
~ 0 _ OMe
OMe
Methyl 3,4-di-O-methyl-l~-D-dbopyranosid-2-O-ate
Anions produced by formal loss of H + from a carbon atom are denoted by the suffix '-ide', with appropriate
locants and a 'deoxy-' prefix if necessary (cf. 2-Carb-31.2).
Examples:
HO\ /CHO
H /CHO
C-I
HOCHI
HCOH
I
HCOH
I
CH2OH
\C-I
HOCHI
HCOH
I
HCOH
I
CH2OH
D-arabino-Hexos-2-C-ide
2-Deoxy-D-arabino-hexos-2-ide
CH2OMe
H~Po
OH.k~
H
-- H
Me
MeO ~1
IJ
YH- - - OMe
r
1,5-Anhydro-2,3,4,6-tetra-O-methyI-D-glucitot-1-ide
62
2-Carb-32.4. Radical ions
Radical ions can be named by adding the suffix 'yl' to ion names. Alternatively, the words 'radical cation'
or 'radical anion' may be added after the name of the parent with the same molecular formula, especially
when the location of the radical ion centre is not to be specified.
Examples:
CH2OH
H H
H
HO' ~ , ~ ¢
H
H, OH
'
OH
D-Glucopyranosiumyl,or D-glucopyranoseradicalcation
CH2OH
H HH
H, OH
H
1
H
°-
2-Deoxy-D-arabino-hexos-2-id-2-yl,or 2-deoxy-D-arabino-hexopyranos-2-ylideneradicalanion
2-Carb-33. Glycosides and glycosyl compounds
2-Carb-33.1. Definitions
Glycosides were originally defined as mixed acetals (ketals) derived from cyclic forms of monosaccharides.
Example:
H O ~
HO
OHm)Me
Methyl tz-D-glucopyranoside
However, the term 'glycoside' was later extended to cover not only compounds in which, as above, the
anomeric hydroxy group is replaced by a group -OR, but also those in which the replacing group is -SR
12
123
(thioglycosides),-SeR (selenoglycosides),-NR R (N-glycosides), or even-CR R R (C-glycosides). 'Thioglycoside' and 'selenoglycoside' are legitimate generic terms; however the use of 'N-glycoside', although
widespread in biochemical literature, is improper and not recommended here ('glycosylamine' is a perfectly
acceptable term). 'C-Glycoside' is even less acceptable (see Note to 2-Carb-33.7). A glossary of terms based
on 'glycose' is given in the Appendix.
Particularly in naturally occurring glycosides, the compound ROH from which the carbohydrate residue has
been removed is often termed the aglycone, and the carbohydrate residue itself is sometimes referred to as
the 'glycone'.
Note. The spelling 'aglycon' is often encountered.
2-Carb-33.2. Glycosides
Glycosides can be named in three different ways:
(a) By replacing the terminal '-e' of the name of the corresponding cyclic form of the monosaccharide by
'-ide' and preceding this, as a separate word (the intervening space is significant), the name of the group R
(see examples below).
Examples:
OEt
~O~~CH2OH
H C O N ~ ~ OMe
I
OH OH
HOCH2
Methyl ~-D-gulofuranoside
not methyl-c~-D-gulofuranoside
HO
Ethyl ~-o-fructopyranoside
63
CHO
M e O ~
HO
Methyl
(6R)-D-gluco-hexodialdo-6,2-pyranoside
Note. This is the 'classical' way of naming glycosides. It is used mainly when the group R is relatively simple (e.g.
methyl, ethyl, phenyl).
(b) By using the term 'glycosyloxy-', in the appropriate form for the monosaccharide, as prefix, for the name
of the compound.
Note. This prefix includes the oxygen of the glycosidic bond. An example is given in 2-Carb-31.2; more are given
below.
(c) By using the term 'O-glycosyl-' as prefix to the name of the hydroxy compound.
Note. This prefix does not include the oxygen of the glycosidic group. This is the appropriate method for naming natural
products if the trivial name includes the OH group. The system is also used to name oligosaccharides (see 2-Carb-37).
Examples:
CH3
ii
COOH
-
.o
I
O.
I
°"
I
v
OH
(20S)-20-Hydmxy-513-pregnan-3a-yl 13-D-glucopyranosiduronic acid
or (20S)-3a-(~-D-glucopyranosyloxyuronic acid)-513-pregnan-20-ol;
for biochemical usage, pregnanediol 3-glucuronide
Note. A common biochemical practice would give the name (20S)-3ct-([3-D-glucopyranuronosyloxy)-5~-pregnan-20ol. This practice of naming glycosyl residues from uronic acids as 'glycuronosyl' is unsatisfactory because it implies
the acceptance of the parent name 'glycuronose'. However the use of a two-word substituent prefix (glycosyloxyuronic
acid), ending with a functional class name, remains inherently problematic, since it contravenes general organic
nomenclature principles [ 13,14]. The latter practice has the advantage of retaining homomorphic relationships between
glycoses and glycuronic acids.
CH2OH
H
O
I \ OH
HO ~ . ~
H/I
C-CH 3
ii
O
H
CH2OH ~
HO .~--,....&;,...~ ,-,
ON
-
OH
H
4-Acetylphenyl 13-D-glucopymnoside
or 4'-(l~-D-glucopyranosyloxy)acetophenone;
trivial name picein
CH2OH
~
(S)-O-~-D-Glucopyranosylmandelonitrile
or (S)-(l~-D-glucopyranosyloxy)(phenyl)acetonitrile;
trivial name sambunigrin
H
..2--,
H
O
H
Ph
OH
OH
7-([3-o-Glucopyranosyloxy)-8-hydroxycoumarin;
trivial name daphnin
H
H
!
1
OH
O3-~-o-XylopyranosyI-L-serine [(Xyl-)Ser]
64
Glycosides can be named as substituents by the methods of 2-Carb-31.
Example:
o
CH2
-)o/
H~~'~H
H OH
o
i('~
"~H °Me
(Methyl 5-deoxy-13-D-xylofuranosid-5-yl) 2-(4-hydroxy-3-methoxyphenyl)-7-methoxy5-[2-(methyl 13-D-xylofuranosid-5-O-ylcarbonyl)vinyl]-2,3-dihydrobenzofu ran-3-carboxylate
2-Carb-33.3. Thioglycosides
Names for individual compounds can be formed, like those for glycosides, in three ways, as follows.
(a) By using the term thioglycoside, preceded by the name of the group R.
(b) With the prefix 'glycosylthio-', followed by the name of the compound RH; this prefix includes the sulfur
atom.
(c) With the prefix 'S-glycosyl-' (not including the S atom), followed by the name of the thio compound.
Sulfoxides and sulfones can also be named by functional class nomenclature [13, 14].
Examples:
,.
CH2OH
H O ~ w , . , , ~ SEt
OH
OH OH
4-(C~-D-Ribofuranosylthio)benzoic acid
or 4-carboxyphenyl 1-thio-c(-D-ribofuranoside
Ethyl 1-thio-13-D-glucopyranoside
OSO3K
CH2OH
I
H)
O~ S--c~/N
E'H
"~J ~CH2~H:CH 2
H
OH
S-13-D-Glucopyranosyl (Z)-O-(potassium sulfonato)but-3-enehydroximothioate
(trivial name sinigrin)
CH2OAc
A c O ~
AcO I
ph/S<'o
Phenyl tetra-O-acetyi-(x-D-glucopyranosyl sulfoxide
or phenyl 2,3,4,6-tetra-O-acetyl-l-thio-~-D-glucopyranoside S-oxide
55
2-Carb-33.4. Selenoglycosides
Names are formed analogously to those for thioglycosides (2-Carb-33.3).
Examples:
H
H
o
H ./~1.
H
!
\ Se--CH2'"'(~-"COOH
I
.o ~__(.
HO.~1~o seto.2120oo.
OH
2-Carboxyethyl 1-seleno-13-D-xylopyranoside
or 3-(13-D-xylopyranosylseleno)propanoic acid
OH
Se-13-o-RibopyranosyI-D-selenocysteine
or (S)-2-amino-2-carboxyethyl 1-seleno-l~-D-ribopyranoside
or 3-(13-D-ribopyranosylseleno)-D-alanine
2-Garb-33.5. Glycosyl halides
Compounds in which the anomeric hydroxy group is replaced by a halogen atom are named as glycosyl
halides. Pseudohalides (azides, thiocyanates etc.) are named similarly.
Examples:
CH2OAc i-,
~ o ~ ~ \
AcO
Br
Tetra- O-acetyl-et-D-mannopyranosyl bromide
COOMe O
AcO~ , , , ~ ' ~ " ~
I
AcO
Br
Methyl (2,3,4-tri-O-acetyi-c(-D-glucopyranosyl)uronate bromide
not methyl 2,3,4-tri-O-acetyl-l-bromo-l-deoxy-(z-D-glucopyranuronate
_
CH2OBn r~
BnO~
1 I~r
"%
3, 4,6-Tri-O-benzyl-cc-D-arabino-hexopyranosyl-2-ulose bromide
CHO
~/C---o~/LB,
~
OBn
BnO
or
3,4,5-Tri-O-benzyl-ct-D-arabino-hexos-2-ulo.2,6-pyranosyl bromide
3,4,5-tri-O-benzyl-aldehydo-~-D.arabino-hexos.2-ulopyranosyl bromide
COOMe
oc o<c,
OAc
~
Methyl
N
/
H ~
OAc
(5-acetamid~4~7~8~9~tetra-~-acety~3~5~dide~xy~g~ycer~-~-D-ga~act~-n~n-2-u~pyran~sy~)~natechloride
66
2-Carb-33.6. N-Glycosyl compounds (glycosylamines)
N-Glycosy! derivatives are conveniently named as glycosylamines. In the case of complex heterocyclic
amines, such as nucleosides, the same approach is used.
Examples:
O
..~
°, OHIO.
o
CHO
OH
H
HO
OH
1-[B-D-Ribofuranosyluracil (trivial name uridine)
N-Phenyl-a-D-fructopyranosylamine
not aniline (z-D-fructopyranoside
CHzOH
,1
o
H/.I
HO~ . . ~
H
o,.
\NH--C'"'C'",'[CH214NH 2
H
NHAc
Nl-(2-Acetamido-2-deoxy-~-D-glucopyranosyl)-L-iysinamide (Lys-NH-GIcNAc)
[trivial name N -(N-acetylglucosaminyl)-L-lysinamide]
NH2
HO
OH
9-(5-S-Methyl-5-thio-~-D-ribofu ranosyl)adenine
COOH
H2N,.---C-.-..H
CH20H
CH2
I
,F----'- O
H/ I
\ NH--C-O
HO~ _ ~
H
H
NHAc
N4-(2-Acetamido-2-deoxy-I~-D-glucopyranosyl)-L-asparagine [(GIcNAc-)Asn]
or 2-acetamido-N1-L-13-aspartyl-2-deoxy-13-o-glucopyranosylamine
(trivial name 13-N-acetylglucosaminyl-L-asparagine)
H°~~HO
NH
I~'~-o~CONH2
HO~.~
OH
HO
Bis((~-D-glucopyranosyluronamide)amine
67
2-Carb-33.7. C-Glycosyl compounds
Compounds arising formally from the elimination of water from the glycosidic hydroxy group and an H atom
bound to a carbon atom (thus creating a C-C bond) are named using the appropriate 'glycosyl-' prefixes (or
other methods as appropriate, avoiding 'C-glycoside' terminology).
Note. The term C-glycoside, introduced for naming pseudouridin¢ (a nucleosid¢ from transfer RNA), is a misnomer.
All other glycosides are hydrolysable; the C-C bond of 'C-glycosides' is usually not. The use and propagation of names
based on 'C-glycoside' terminology is therefore strongly discouraged.
Example:
jN--~
HsN--~N
CH20H
COOH
HO?H~jO " , ~ T
OH
HO
4-13-D-Glucopyranosylbenzoicacid
not 4-carboxyphenyl C-~-D-glucopyranoside
NH
H
8-(2-Deoxy-~-D-erythro-pentofuranosyl)adenine
not adenine 8-(2-deoxyriboside)
O
HN"JLNH
HOCH2
O
H
H
HO
OH
5-~-D-Ribofuranosyluracil; trivial name pseudouridine
CH2OH
OH
3,7-Anhydro-2-deoxy-D-glycero-D-gulo-octononitdle
or 2- C-(~-o-glucopyranosyl)acetonitrile
not cyanomethyl C-~-D-glucopyranoside
CH2OH.,HO~
Ho"~'--~
HO
OH
O
I.
II
~
i
Jl
OH 0
OH
II
~
I
OH
2-~-D-Glucopyranosyl-1,3,6,7-tetrahydroxyxanthen-9-one;trivial name mangiferin
OH O
H , "O~ C H 2
OH
OH
O"~/OH
HOCH2~L~
I HO
HO
(10S)-10-13-D-Glucopyranosyl-1,8-dihydroxy-3-(hydroxymethyl)anthracen-9(10H)-one;
trivial names aloin A, (10S)-barbaloin
68
OH
CH2oH.o o.
OH
°"
O
6-i~-D-Glucopyranosyl-4',5,7-trihydroxy-8-Ot-L-rhamnopyranosylflavone;
trivial name violanthin
2-Carb-34. Replacement of ring oxygen by other elements
2-Carb-34.1. Replacement by nitrogen or phosphorus
Names should be based on those of the amino sugars (see 2-Carb-14) (or the analogous phosphanyl sugars)
with the amino or phosphanyl group at the non-anomeric position. Ring-size designators (furano, pyrano etc.)
are the same as for the oxygen analogues.
Examples:
CHzOH H
H
O
~
_
nu
-OH
5-Amino-5-deoxy-D-glucopyranose; trivial name nojirimycin
CH2OH H
N
HO~..~.'~..~
1-Amino-1,5-anhydro-1-deoxy-D-mannitol or 1,5-dideoxy-1,5-imino-D-mannitol;
trivial name deoxymannojirimycin
Note the extension of the use of 'anhydro' in the above example to include the elimination of water between
-NH2 and -OH (cf. 2-Carb-26).
Et
CH20H /
H
HO
oH
ON
5-Deoxy-5-ethylamino-et-D-glucopyranose
5-Deoxy-5-phosphanyl-o-xylopyranose
Note. Use of the terms 'aza sugar', 'phospha sugar' etc. should be restricted to structures where carbon, not oxygen, is
replaced by a heteroatom. Thus the structure below is a true aza sugar. The term 'imino sugar' may be used as a class
name for cyclic sugar derivatives in which the ring oxygen atom has been replaced by nitrogen.
CH2OH O
HoT
OMe
Methyl 3-deoxy-3-aza~-D-ribo-hexopyranoside
2-Carb-34.2. Replacement by carbon
The (non-detachable) prefix 'carba-' signifies replacement of a heteroatom by carbon in general natural
product nomenclature [26], and may be applied to replacement of the hemiacetal ring oxygen in carbohydrates
if there is a desire to stress homomorphic relationships. If the original heteroatom is unnumbered, the new
carbon atom is assigned the locant of the non-anomeric adjacent skeletal atom, with suffix 'a'.
69
Note. The draft natural product rules [26] recommend that the new carbon atom takes the locant of the lower-numbered
proximal atom. However, carbohydrate chemists regard the ring oxygen as formally originating from the non-anomeric
(usually higher-numbered)position.
Additional stereochemistry (if any) at the new carbon centre is specified by use of the R/S system ([ 13], Section
E).
Structures of this type can also be named as cyclitols [8].
Examples:
CH2OH5a
HO~k'-'---KZ"~
HO.~.~
"OH
OH
5a-Carba-I~-D-glucopyranose
O
HN~,
oJ .JJ
HO
CHa
H
1-(2-Deo~-4a-carba-f3-D-er~hm-pentofuranosyl)thymine
or 4'a-carbathymidine
CH2OH sa
5a
HO
O
H
.oCH3
5a-Carba-~-D-fructofuranosyl 5a-carba-~-D-glueopyranoside
O
HO
H
1-[(4aS)-2-Deoxy-4a-fluoro-4a-carba-I]-D-erythro-pentofuranosyl]thymine
or (4'aS)-4'a-fluoro-4'a-carbathymidine
2-Carb-35. Carbohydrates containing additional rings
Internal bridging of carbohydrate structures by bivalent substituent groups creates additional rings, which can
be named either by use of a substituent prefix representing the bridging group, or by fusion nomenclature.
The following recommendations for the use of these two approaches are not thoroughly developed; they
simply represent an attempt to rationalize and codify current literature practice in the use of systems not in
general well suited to carbohydrate applications. Bridging substituent prefix nomenclature (2-Carb-35.1) is
based on the system well established for simple cyclic acetals (2-Carb-28), and fusion nomenclature
(2-Carb-35.2) on current literature usage and requirements for general natural product nomenclature [26].
70
2-Carb-35.1. Use of bivalent substituent prefixes
Where the new bridge is attached to oxygen (or a replacement heteroatom, e.g. nitrogen in an amino sugar)
already indicated in the name of the unbridged carbohydrate, the bivalent substituent prefix denotes
substitution at two heteroatoms as outlined in 2-Carb-24.1 and 2-Carb-25 [method (b)]. Heteroatoms not
directly bonded to the carbohydrate chain are regarded as part of the bridge.
Where the new bridge is attached through C-C bonds to the carbohydrate chain, the bridge prefix denotes a
double C-substitution. Procedures are as outlined in 2-Carb-16.
Examples:
S
0 ........
t
O~..-CH20H
"
.
0
I
2,3:4,5-Di-O-isopmpylidene-~-D-fructopyranose
Note 1. The alternative fusion name (see 2-Carb-35.2) is 2,2,2",2"-tetramethyl-4,4",5,5"-tetrahydro-(2,3,4,5-tetradeoxy~3-D-fmctopyranoso)[2,3-d:4,5-d']bis[ 1,3]dioxole; this is clearly less desirable on grounds of complexity.
Note 2. The use of prefixes ending in '-ylidene' for gem-bivalent substituent groups is traditional in the carbohydrate
field, although no longer recommended in general organic nomenclature [ 14].
CH3--COOMe
o
kOH o ~ O M e
Methyl [(S)-4,6-O-(1-methoxycarbonylethylidene)]-J3-D-mannopyranoside
HO~OMe
CH2OH~
Methyl 2,3-(butane-l,4-diyl)-2,3-dideoxy-~-D-glucopyranoside
Note. The alternative fusion name (see 2-Carb-35.2) is hexahydro(methyl 2,3-dideoxy-13-D-glucopyranosido)[2,3]benzene
Methyl 2,3-(buta-l,3-diene-l,4-diyl)-2,3-dideoxy-~-D-erythro-hex-2-enopyranoside
Note. The alternative fusion name (see 2-Carb-35.2) is (methyl 2,3-dideoxy-~-D-erythro-hexopyranosido)[2,3]benzene
H2C
O
1,6-Anhydm-2,3-dideoxy-2,3-(9,10-dihydroanthraeene-9,lO-diyl)-~-D-ribo-hexopyranos-4-ulose
71
BnOCH2
o
~
(lS)-l,5-Anhydro-3,4,6-tri-O-benzyl-l-C,2-O-(o-phenylenemethylene)-D-mannitol
Note. The isomeric chromene would be named as a 2-0,1-C-substituted system.
The prefix 'cyclo-' may be used for a single-bond bridge [14].
Examples:
AcN-NH
AcO-~~
OAcI
OMe
Methyl 4-N-acetyl-2,3-di-O-acetyl-4,6-diamino-4,6-N-cyclo-4,6-dideoxy-c(-D-galactopyranoside
~
AcO
OMe
OAc
Methyl 2,3-di-O-acetyl-4,6-cyclo-4,6-dideoxy-~D-galactopyranoside
2-Carb-35.2. Ring fusion methods
Fusion methods are employed as in general natural product nomenclature [26], except that the original
carbohydrate ring is cited first, in parentheses (with terminal '-e', if present, replaced by '-o'). For designating
stereochemistry, bonds in the new ring are considered as equivalent to OH, unless OH (or its equivalent) is
still present at the ring junction. Substituents on the carbohydrate portion are included within the parentheses
enclosing the fusion prefix. Substituents on the new ring (including 'hydro-' prefixes) precede the carbohydrate term(s). If there is a choice, the new ring is numbered in the direction used to define the fusion locants.
Note. General natural product fusion nomenclature [26] would require the carbohydrate portion to be cited last (e.g.
oxazoioglucopyranose), whereas it is cited first here and in the literature.
Examples:
CH2OHc~
ph, ~ 0
2-Phenyl-4,5-dihydro-(1,2-dideoxy-~-D-glucopyranoso)[2,1-dJ-1,3-oxazole
Note 1. The alternative name using a substituent prefix (see 2-Carb-35.1) is 2-amino-lrO,2-N-(benzylylidene)-2-deoxy-o~-D-glucopyranose.
Note 2. Literature fusion names for this type of compound use 'glucopyrano[2,1-d]oxazoline' terminology. However,
names for partially hydrogenated heterocycles ending in 'oline' were abandoned by IUPAC in 1983 [27], in favour of
'dihydro......ole'. Use of 'pyranoso' rather than 'pyrano' is recommended to avoid confusion with the normal fusion
prefix from 'pyran' and to simplify rules for naming derivatives (e.g. glycosides).
CHzOAc
ACO~o
MeNH-2-Methylamino-4,5-dihydro-(3,4,6-tri-O-acetyl-1,2-dideoxy-cc-D-glucopyranoso)[2,1-o1-1,3-oxazole
Note. The alternative name using a substituent prefix (see 2-Carb-35.l) is 3,4,6-tri-O-acetyl-2-amino-2-deoxy-l-O,2N- [(methylamino)methylylidene]-~-D-glucopyranose.
72
CH2OHc~
H O / - ~
HO
HN I
NPh
~
O
3-Phenyltetrahydro-(1,2-dideoxy-(z-D-glucopyranoso)[1,2-d]imidazol-2-one
Note. The alternative name using a substituent prefix (see 2-Carb-35.1) is 2-amino-1,2-N-carbonyl-l,2-dideoxy-l-Nphenyl-(x-D-glucopyranosylamine
CH3
N' o
A c O ~
CH3
2-Methyl-5,6-dihydm-(4-O-acetyl-1,2,3,6-tetradeo~- 3-methyl-~-t.-ribo-hexopyranoso)[3,2,1-Oo]-4H-1,3-oxazine
Note 1. The alternative name using a sabstituent prefix (see 2-Carb-35.1) is 4-O-acetyl-3-amino-2,3,6-trideoxy-1-O,3N-(ethan- 1-yl- 1-ylidene)-3-C-methyl-o~-L-ribo-hexopyranose
Note 2. This example would net normally be regarded as a fused system for nomenclature purposes, since it is net orthoor ortho- and peri-fused [13].
2-Carb-35.3. Spire systems
Spiro systems can be named by normal procedures [13]. For clarity, any anhydro or deoxy prefixes or
chalcogen replacement prefixes (e.g. thio) referring to the spiro junction should appear next to the carbohydrate stem. The carbohydrate component is cited first. Configuration at the spiro junction is assigned by the
R,S system.
Example:
A c O ' _~ CH2OAc
" ~ ~
Ph
(1 N)-2,3,4,6-Tetra-O-acetyl-3"-phanylspiro[1,5-anhydro-D-glucitol-1,5'-[1,4,2]exathiazele]
~
N'~oH O""--CMe2
(3S)-5-OLBenzoyl-l',2'-dihydro-1,2-O-isopropylidenespiro[3-deoxy-o~-D-eOfthro-pentofuranose-3,3"naphtho[1,2-e][1,3]oxazin]-2'-ol
The following spiro disaccharide example is best named by use of a gem-bivalent substituent prefix:
CH2OH
O O
H
Me
HOCH2*" y
~OH
OH
Methyl 2,3-O-D-glucopyranosylidene-c(-D-mannopyranoside
73
Stereochemistry at C-1 of the glucose residue could be indicated as R or S, e.g. [(1R)-2,3-O-D-glucopyranosylidene] .....
2-Carb-36. Disaccharides
2-Carb-36.1. Definition
A disaccharide is a compound in which two monosaccharide units are joined by a glycosidic linkage.
2-Carb-3.6.2. Disaccharides without a free hemiacetai group
Disaccharides which can be regarded as formed by reaction of the two glycosidic (anomeric) hydroxy groups
with one another are named, systematically, as glycosyl glycosides. The parent (cited as the 'glycoside'
component) is chosen according to 2-Carb-2.1. Both anomeric descriptors must be included in the name.
Examples:
CH2OH c~
CH2OH ,-,
o
H° --Z""~'.O~
I
CH2OH
CH20H
OH
c~-t)-Glucopyranosyl et-o-glucopyranoside
[c(-D-Glcp-(1 ~-->1)-~t-D-Glcp]
(trivial name (z,(~-trehalose)
13-o-Fructofuranosyl (x-b-glucopyranoside
[13-D-Fruf-(2~-)1 )-a-D-Glcp]
not a-o-glucopyranosyl 13-D-fructofuranoside
(trivial names sucrose, saccharose)
Note. Such disaccharides are also known as non-reducing disaccharides.
If derivatives are named on the basis of the trivial name, the component cited first in the systematic name
receives primed locants.
Example:
Example:
CI CH2CI O
l
HO
CH2OH
4,6,6'-Trichloro-4,6,6'-trideoxygalactosucrose
or 6-chloro-6-deoxy-13-b-fructofuranosyl 4,6-dichloro-4,6-dideoxy-ct-D-galactopyranoside
('galactosucrose' is a trivial name for the 4-epimer of sucrose)
2-Garb-36.3. Disaccharides with a free hemiacetal group
A disaccharide in which one glycosyl unit has replaced the hydrogen atom of an alcoholic hydroxy group of
the other is named as a glycosylglycose. The locants of the glycosidic linkage and the anomeric descriptor(s)
must be given in the full name.
There are two established methods in use for citing locants: either in parentheses between the glycosyl and
glycose terms, or in front of the glycosyl prefix, as in the names of glycosides. The former (preferred) method
is derived from that used to designate residues in oligosaccharides (see 2-Carb-37 and -38).
Note. The latter method is that used by Chemical Abstracts Service for disaccharides.
The O-locants used for the former method in the previous recommendations [1] are omitted here.
74
Examples:
CH2OH
HO
c,m° o
H
O
~
X
OH
O
~
H
CH2OH
~
O
~
OH I
OH
OH
C~-D-Glucopyranosyl-(1-~4)-~-D-glucopyranose
[(Z-D-Glcp-(1--~4)-~-D-Glcp]
or 4-O-c~-D-glucopyranosyl-~-D-glucopyranose
(trivial name J~-maltose, not J3-D-maltose)
~-D-Galactopyranosyl-(1 ~4)-(~-D-glucopyranose
[~-D-Galp-(1-->4)-(z-D-Glcp]
or 4-O-~-D-galactopyranosyl-o~-D-glucopyranose
(trivial name c~-Iactose, not co-D-lactose)
HO
LCH2OHj O
CH2OH o
HO
-
AohH-'-,,~OH
13-o-Galactopyranosyl-(l~4)-N-acetyI-D-glucosamine (trivial name N-acetyllactosamine; kacNAc)
Note. Disaccharides with a free hemiacetal group are also known as reducing disaccharides.
2-Carb-36.4 Trivial n a m e s
Many of the naturally occurring disaccharides have well established trivial names. Some of these are listed
below, together with the systematic names in both versions (see above).
Cellobiose
J3-D-Glucopyranosyl-(l--)4)-D-glucose
4- O-~-D-GlucopyranosyI-D-glucose
Gentiobiose
~-o-Glucopyranosyl-(l~6)-D-glucose
6-O-~-o-Glucopyranosyl-D-glucose
Isomaltose
(Z-D-Glucopyranosyl-(1~6)-D-glucose
6-O-c~-D-GlucopyranosyI-D-glucose
Melibiose
C~-D-Galactopyranosyl-(1--~6)-D-glucose
6- O-c~-D-GalactopyranosyI-D-glucose
Primeverose
~-o-Xylopyranosyl-(1--~6)-D-glucose
6-O-~-D-XylopyranosyI-D-glucose
Rutinose
C~-L-Rhamnopyranosyl-(1--~6)-D-glucose
6-O-~-L-RhamnopyranosyI-D-glucose
The systematic names of trehalose, sucrose, maltose and lactose have been given already (with the formulae).
If derivatives are named on the basis of the trivial name, the component cited first in the systematic name
receives primed locants.
Example:
CH2OTsO
CH2OAc
A c O ' ~ A c O - ~
AcO
Ac'O I
OAc
1,2,2',3,3',4',6-Hepta- O-acetyl-6'-O-tosyl-c~-cellobiose
or 2,3,4-tri-O-acetyl-6-O-tosyl-J3-D-glucopyranosyl-(1 --~4)-1,2,3,6-tetra-O-acetyl-ec-D-glucopyranose
If the reducing terminal is a uronic ester glycoside, the ester alkyl group is cited at the beginning of the name,
and the aglyconic alkyl group is cited with the name of the glycosidic residue.
75
Example:
COOMe
? ~ O C H 2 C H
CH30Ac~~OMe
=OH2
gzO
MeO
Methyl (3-O-acetyl-6-deoxy-2,4-di-O-methyl-¢-L-galactopyranosyl)-(1->4)-(allyl
~-o-glucopyranosid)uronate
2,3-di-O-benzoyl-
2-Carb-3 7. Higher oligosaccharides
2-Carb-37.1. Oligosaccharides without a free hemiacetal group
Trisaccharides (for example) are named as glycosylglycosyl glycosides or glycosyl glycosylglycosides as
appropriate. A choice between the two residues linked through their anomeric positions for citation as the
'glycoside' portion can be made on the basis of 2-Carb-2.1. Alternatively, a sequential (end-to-end) naming
approach may be used, regardless of 2-Carb-2. I. The names are formed by the preferred method of naming
disaccharides (see 2-Carb-36.3): the locant of the anomeric carbon atom, an arrow, and the locant of the
connecting oxygen of the next monosaccharide unit are set in parentheses between the names of the residues
concerned.
Examples:
HO
OCH2
O
?
I
OH
-
CH2OH
~-D-Fructofuranosyl C¢-D-galactopyranosyl-(1--)6)-CeD-glucopyranoside'
(glucose preferred to fructose for citation as 'glycoside')
or ¢-D-galactopyranosyl-(1--~6)-¢-D-glucopyranosyl ~-o-fructofuranoside
(sequential method)
[C¢-D-Galp-(1--)6)-c¢-D-Glcp-(1<-~2)~-D-Fruf ]
(trivial name raffinose)
76
Ho~O\
HOCH2
o
O.
HO
HOCH2
I
H I
O
O~
I
O
HOCH2 _O.
He
I
H
~-D-Fructofu ranosyl-(2-,1)-13-D-ffuctofu ranosyl-(2~ 1)-13-D-fruetofuranosyl ~-D-glucopyranoside
[13-D-Fruf-(2--~l)ff3-D-Fruf-(2~l)-f3-D-Fruf-(2~-~l)-~-D-Glcp] (trivial name ngstose)
If derivatives are to be named on the basis of the trivial name, the component cited last in the systematic name
receives locants with no primes, the preceding component singly-primed locants, etc. However, naming of
trisaccharide and higher oligosaccharide derivatives systematically is preferred, to avoid ambiguity.
2-Carb-37.2. Oligosaccharides with a free hemiacetal group
An oligosaccharide of this class is named as a glycosyl[glycosyl]nglycose, i.e. the reducing sugar is the parent.
Anomeric descriptors and locants are given as described in 2-Carb-37.1. The conventional depiction has the
reducing sugar (glycose residue) on the right and the non-reducing end (glycosyl group) on the left. Internal
sugar units are called glycosyl residues (the term 'anhydrosugar unit' is misleading and its use is discouraged).
As the reducing end is often converted into the corresponding alditol, aldonic acid or glycoside derivative,
the more general term 'downstream end' has been proposed for this end of the molecule.
Examples:
CH2OH n
HO-.~"- ~OH
OCH2
Ho
\
CH2OH ,..,,
~-D-Glucopyranosyl-(l~6)-CC-D-glucopyranosyl-(l~4)-D-glucopyranese (trivial name panese)
CH2OH
H O " ~ ~ ~
CH2OH
Ho ~k,.......-"~-~.~ O ~
~
OH
~,
A \
glycosyl group
HO~ " ~ . . . ~ O N
glycosylresidue
O~
CH2OH
~X\
HO-4~,,,,,,~ Nk~'~
n ~
OH
glycose residue
OH
~-o-Glucopyranosyl-(1 -->4)-13-D-glucopyranosyl-(1--~4)-D-glucopyranose (trivial name cellotriose)
77
NaOOC HO
CH2OH
Ac .
O
~
\
L \O ~'~
HO
o
\__OMe
HO
Methyl (sodium (~-L-idopyranosyluronate)-(1 -~4)-(2-acetamido-2-deoxy-~-o-glucopyranosyl)-(1 --)4)(sodium 13-D-glucopyranosyluronate)-(l--)3)-~D-galactopyranoside
{Na2[(~-L-IdopA-(1 --)4)-C(-D-GlcpNAc-(1--)4)-13-D-GlcpA-(1---)3)-13-D-GalpOMe]}
Higher oligosaccharides are named systematically in the same way. However, it is often preferable to give
their structures by use of the symbolic approach outlined in 2-Carb-38).
Trivial names for linear oligosaccharides consisting only of 1---~4 linked (Z-D-glucopyranosyl residues are
maltotriose, maltotetraose etc. Similar names, based on the component sugar, are convenient for referring to
other homo-oligosaccharides (e.g. xylobiose, galactotetraose), but such names should be used sparingly.
Locants for naming substituted derivatives may be obtained by assigning roman numerals to the residues in
ascending order starting from the reducing end.
Example:
CH2OTrr,
OH
CH2OH
,v
OH
CH2OHr~
'"
c. oH
"
61V-O-Tritylmaltotetraose
Arabic numerals have also been used in this context, but confusion may result when component sugar residues
have structural modifications (e.g. chain branches) requiring superscript locant numbers. The present
recommendation follows long-established usage in glycolipids [21].
2-Carb-37.3. Branched oligosaccharides
Terms designating branches shou|d be enclosed in square brackets. In a branched chain, the longest chain is
regarded as the parent. If two chains are of equal length the one with lower locants at the branch point is
preferred, although some oligosaccharides are traditionally depicted otherwise, such as the blood group A
trisacchande exemplified below.
Examples:
CH2OH r~
CH2OH r~
HOO ~ D ~
H
I
6
'~CH2
OH
(z-o-Glucopyranosyl-(1 --+4)-[C~-D-glucopyranosyl-(1--)6)]-D-glucopyranose
[or 4,6-di-O-(o¢-D-glucopyranosyl)-D-glucopyranose]
(trivial name isopanose)
78
OH
COOH
HO
CH2OH
HOOH~X__~~' L~°"o c.~o.
HO[
OH
AcNH
%H
HaC~~oH
I oH
HO
(5-Acetamido-a,5-dideo~-D-glycoro-~-D-galacto-non-2-ulopyranosylonic acid)-(2--*a)-13-D-galactopyranosyl-(l~a)-
[~-L-fucopyranosyl-(1~ 4 )]-2-acetamido-2-deoxy-D-glucopyranose
or 5-N-acetyl-~-neuraminyl-(2~3)-~-D-galactopyranosyl-(1--~3)-[~4.4ucopyranosyl-(1--*4)l-2-acetamido-2-deoW-Dglucopyranose
{~-NeupSAc-(2~3)-~-D-Galp-(1~3)-[c~-k-Fucp-(1~4)]-D-GlcpNAc}(sialyl-kea trisaccharide)
HO
L CH2OH O
H
~
HO
o ~"~°"~°
HO
2-Acetamido-2-deoxy-~-D-galactopyranosyl-(1 -->3)-[{Z-L-fucopyranosyl-(1 -->2)]-D-galactopyranose
{(Z-D-GalpNAc-(1-->3)-[~-L-Fucp-(1-->2)]-D-Galp} (blood group A trisaccharide)
2-Carb-37.4. Cyclic oligosaccharides
37.4.1. Semisystematic names
Cyclic oligosaccharides composed of a single type of oligosaccharide unit may be named semisystematically
by citing the prefix 'cyclo', followed by terms indicating the type of linkage [e.g. 'malto' for o~-(1--->4)-linked
glucose units], the number of units (e.g. 'hexa' for six) and the termination Lose'. The trivial names
(z-cyclodextrin ((z-CD) for cyclomaltohexaose, ~-cyclodextrin ([3-CD) for cyclomaltoheptaose and 7-cyclodextrin (y-CD) for cyclomaltooctaos¢ arc well established.
Example:
CH2OHO
°~oo.°~
HOH C ) -
HoHo
HOH2O
~oOH
(';%.,o.
i OH .,,~OH HO-J I
~-~_z~o-.z~o
0
CH20H
Cyclomaltohexaose (c~-cyclodextrin, c~-CD)
79
Structures with linkages other than (1---~) should be named systematically (see 2-Carb-37.4.2).
Note. The cyclic oligosaccharides arising from enzymic transglycosylation of starch have been referred to as Schardinger dextrins. These names (and those of the cyclohexaamylose type) are not recommended, but the abbreviation CD
is tolerated.
Derivatives with the same substitution pattern on each residue can be named semisystematically by assigning
a single multiplicative prefix (e.g. hexakis, heptakis etc.) to the substituent prefixes as a group.
Example:
I
r- O~?
o~CH21Me
OMe
Heptakis(6-deoxy-6-iodo-2,3-di-O-methyl)cyclomaltoheptaose
Derivatives with different substitution patterns on the various residues can be named by the method of
2-Carb-37.2, assigning a roman numeral to each residue.
CH2NH20
Example:
\ OH .,~--OH HO--/ I
O
CH20H
61-Amino-6Ldeoxycyclomaltohexaose
37.4.2. Systematic names
Cyclic oligosaccharides composed of a single type of residue can be named by giving the systematic name
of the glycosyl residue, preceded by the linkage type in parentheses, preceded in turn by 'cyclo-' with a
multiplicative suffix (i.e. 'cyclohexakis-' etc.)
Examples:
o
OH
7
Cycloheptakis-(1--~4)-(6-deoxy-ec-o-g/uco-heptopyranosylurononitrile)
OH
Cycloheptakis-(1 --~4)-(7-amino-6, 7-dideoxy-(z-D-gluco-heptopyranosyl)
80
The 1--->6 isomer of cyclomaltohexaose should be named cyclohexakis-(1--~6)-~-D-glucosyl, rather than
cycloisomaltohexaose.
2-Carb-37.5. Oligosaceharide analogues
Structures in which the linking glycosidic oxygen is replaced by -CH2- may be named by use of the
replacement prefix 'carba-' (cf. 2-Carb-34.2) for emphasis of homomorphic relationships. The oxygen
replaced is given the locant of the carbon atom to which it is attached in the residue with the lower roman
numeral (cited as superscript) (cf. 2-Carb-37.2), with suffix 'a'.
Example:
.o1
III
CCI2~ HO
HO
ii
HU ~ J ~ - CH20H
0
0 ~ HO'~oH
0
I
OH
411a,411a-Dichloro-411a-carba-(x-maltotriose
If the glycosidic oxygen link is replaced by -O-NH-, normal amino sugar nomenclature can be employed.
Example:
O-~.
OH3
Ho I
OH
4~(2~6~Dide~x~4-thi~-~-D-arabin~-hex~pyran~sy~xVamin~)~4~6~dide~xy-~-~-g~u~pyran~se
2- Carb-38. Use of symbols for defining oligosaccharide structures*
2-Carh-38.1. General considerations
Oligosaccharide and polysaccharide structures occur not only in free form but often as parts of glycopeptides
or glycoproteins [11] or of glycolipids [21]. It can be cumbersome to designate their structures by using the
recommendations of 2-Carb-37. The use of three-letter symbols for monosaccharide residues is therefore
recommended. With appropriate locants and anomeric descriptors, long sequences can thus be adequately
described in abbreviated form.
Symbols for the common monosaccharide residues and derivatives are listed in Table 2. They are generally
derived from the corresponding trivial names. Abbreviations for substituents (see 2-Carb-1.16.2), preceded
by locants, follow the monosaccharide abbreviations directly.
2-Carb-38.2. Representations of sugar chains
For writing the structure of an oligo- or poly-saccharide chain, the glycose residue [the 'reducing group', i.e.
the residue with the free hemiacetal group or modification thereof (e.g. alditol, aldonic acid, glycoside)] should
be at the right-hand end. Also, when there is a glycosyl linkage to a non-carbohydrate moiety (e.g. protein,
peptide or lipid) the glycosyl residue involved should appear at the right.
Numbering of monosaccharide units, if desired, should proceed from right to left.
2-Carb-38.3. The extended form
This is the form employed by the carbohydrate databank CarbBank, and is preferred for most purposes. Each
symbol for a monosaccharide unit is preceded by the anomeric descriptor and the configuration symbol. The
*
The recommendations presented here are a modified version of the published 1980 recommendations [6].
81
Table 2. Symbols for monosaccharide residues and derivatives in oligosaccharide chains
Abequose
Abe
Iduronic acid
IdeA
AIIose
All
Lyxose
Lyx
Altrose
AIt
Mannose
Man
Apiose
Api
Muramic acid
Mur
Arabinose
Are
Neuraminic acid
Neu
Arabinitol
Are-el
N-Acetylneuraminic acid
Neu5Ac
2-Deoxyribose
dRib
N-Acetyl-2-deoxyneur-2-enaminic acid
Neu2en5Ac
Fructose
Fru
N-Glycoloylneu raminic acid
Neu5Gc
Fucose
Fuc
3-Deoxy-D-manno-oct-2-ulosonicacid
Kdo
-Fucitol
Fuc-ol
Rhamnose
Rha
Galactose
Gel
3,4-Di-O-methylrhamnose
Rha3,4Me2
Galactosamine
GaIN
Psicose
Psi
N-Acetylgalactosamine
GalNAc
Quinovose
Qui
~-D-Galactopyranose 4-sulfate
J]-D-Galp4S
Ribose
Rib
Glucose
GIc
Ribose 5-phosphate
Rib5P
Glucosamine
GIcN
Ribulose
Ribulo (or Rul)
2,3-Diamino-2,3-dideoxy-D-glucose
GIcN3N
Sorbose
Sor
Glucitol
GIc-ol
Tagatose
Tag
N-Acetylglucosamine
GIcNAc
Talose
Tel
Glucuronic acid
GIcA
Xylose
Xyl
Ethyl glucopyranuronate
GlcpA6Et
Xylulose
Xylulo (or Xul)
Gulose
Gul
2-C-Methylxylose
Xyl2CMe
Idose
ldo
ring size is indicated by an italicf for furanose o r p for pyranose, etc. The locants of the linkage are given in
parentheses between the symbols; a double-headed arrow indicates a linkage between two anomeric positions.
In CarbBank, omission of t7./t3, D/L, orf/p means that this structural detail is not known.
Examples:
C¢-D-Galp-(1-->6)-cc-o-Glcp-(1<->2)-~-D-Fruffor raffinose (see 2-Carb-37.1)
~-o-Glcp-(1-->4)-~-o-Glcp-(1-->4)-D-GIc for cellotdose (see 2-Carb-37.2)
Branches are written on a second line, or in brackets on the same line.
Example:
~-o-Glcp
i
$
6
oc-O-Glcp-(1-~4)-D-GIc
or CC-D-Glcp-(1-->4)[C~-D-Glcp-(1-->6)]-o-GIc
not
¢-o-Glcp
1
J,
4
c¢-D-GIcp-(1--+6)-o-GIc
(see [11], 2-Carb-37.3)
for 4,6-Di- O-c¢-D-glucopyranosyI-D-glucose
82
The hyphens may be omitted, except that separating the configurational symbol and the three-letter symbol
for the monosaccharide.
2-Carb-38.4. The condensed form
In the condensed form, the configurational symbol and the letter denoting ring size are omitted. It is understood
that the configuration is D (with the exception of fucose and iduronic acid which are usually L) and that the
rings are in pyranose form unless otherwise specified. The anomeric descriptor is written in the parentheses
with the locants.
Example:
Gal(al-6)Gle(a1-2J3)Fru/for raffinose
For most purposes, the short form (2-Carb-38.5) is preferred when abbreviation of the extended form is
desirable.
2-Carb-38.5. The short form
For longer sequences, it is desirable to shorten the notation even further by omitting (i) locants of anomeric
carbon atoms, (ii) the parentheses around the locants of the linkage and (iii) hyphens (if desired). Branches
can be indicated on the same line by using appropriate enclosing marks (parentheses, square brackets etc.).
Whenever necessary, configuration symbols and ring size designators etc. may be included, to make the
notation more specific.
Example:
Gala-6GIca-~SFruf or Gala6GIca~Fruf for raffinose
The following examples show all three representations of the same structure:
(a) extended form
I~-D-Galp-(1-->4)-13-D-GlcpNAc-(1--~2)-a-D-Manp-(1 -->
3
1"
1
a-L-Fucp
(b) condensed form in two lines
Gal(131-4)GlcNAc(l~1-2)Man(a1Fuc(al-3)
or in one line
Gal(131-4)[Fuc(a1-3)]GIcNAc(131-2)Man(a1(c) short form
Gall3-4(Fuca-3)GIcNAcl3-2Manaor Gal134(Fuca3)GIcNAc132Manaor Gal134GlcNAc132ManaFuca3
This last version is recommended as the most explicit representation of branching using the short form.
Note. These representations do not follow the recommendations for choice of main chain given in 2-Carb-37.3. Such
deviations are common in depicting series of naturally occurring oligosaccharides where it is desirable to show
homomorphic relationships.
83
2-Carb-39. Polysaccharides*
2-Carb-39.1. Names for homopolysaccharides
A general term for a polysaccharide (glycan) composed of a single type of monosaccharide residue is obtained
by replacing the ending '-ose' of the sugar name by '-an'.
Note. Examples of established usage of the '-an' ending are: xylan for polymers of xylose, mannan for polymers of
mannose, and galactan for polymers of galactose. Cellulose and starch are both glucans, as they are composed of glucose
residues.
2-Carb-39.2. Designation of configuration of residues
When the configurational series of the monomer residues is known, D- or L- may be included as a prefix to
the name.
Examples:
[4)-o~-D-Glcp-(1--)3)-~-o-Glcp-(1 ~]n
A D-glucan (nigeran)
[5)-~.-L-Araf-(1 --~5)-O~-L-Araf-(1--~5)-c~-L-Araf-(1-~5)-~-L-Araf-(l~]n
3
3
1"
1"
1
(Z-L-Araf
1
~-L-Araf
An L-arabinan (more specifically an et-L-arabinan)
2-Carb-39.3. Designation of linkage
When the major linkage in a homopolysaccharide is known, it may be indicated in the name. The linkage
designation shows the carbon atoms involved in the glycosidic bonds. When specific sugars are designated,
notation for glycosidic linkages should precede the symbols designating the configuration of the sugar; thus,
(1--->4)-tX-D-glucan.
Examples:
HO
HOH2C~~OH
HO
0
(2-~l)-~-D-Fructofuranan (inulin has this structure, with a terminal ~t-D-glucopyranosyl group)
[4)-ct-D-Glcp-(1 "-)]n
(1-~4)-c¢-D-Gulcopyranan
(amylose)
Note. When the linkage between monosaccharide units is non-glycosidic (as in the phosphate derivative shown below),
use of the glycan terminology is inappropriate; other methods of polymer nomenclature should be employed [20].
*
This is a modified version of the 1980 recommendations on polysaccharide nomenclature [7].
84
F
H H H
~
H'~- OCH2~O~ ?--CH2--CHSHSH-CH2-O--I~_-~-OH
L
HO
OH
Jn
Poly[(13-D-ribofuranosyl-5- O-yl) (1 -deoxy-D-ribitol-1 - C,5- O-diyl) (oxidophosphoryl)]
[5)@o-Ribf-(1--)l)-D-Rib-ol-5-P-(O--)]n
Such structures do not conform to the original strict definition of 'polysaccharide' but are generally classified
as polysaccharides in current practice.
2-Carb-39.4o Naming of newly discovered polysaccharides
Names assigned to newly discovered polysaccharides should end in '-an'.
Examples:
[6)-I~-D-Glcp-(1--)]n
Pustulan (a glucan from the lichen Umbilicada pustulata)
F
CH2OH
OH
CH2OH
[ HO'~-~-~q HO7 ~ . - ~ 0 ~ ' - ~ - R H3C..>"
!
L
o.
CO
H
o.
.o
7
IOH
yl
.o j .
[3)-I3-D-Glcp-(1---)4)-13-D-GlcpA-(1 ---)4)-13-D-Glcp-(1--)4)-e~-L-Rhap-(1 --)]n
Gellan (a bacterial polysaccharide originally designated S-60)
Note. The name ending in '-an' refers to the unsubstituted polysaccharide. Thus xylan occurs in nature in unacetylated
and partially acetylated forms. Xylan designates the unacetylated material, and xylan acetate an acetylated derivative.
Well established names such as cellulose, starch, inulin, chitin, amylose and amylopectin are retained.
'Carrageenan' and 'laminaran' are now often used rather than the older names ending in '-in'.
2-Carb-39.5. Uronie acid derivatives.
A polysaccharide (glycan) composed entirely of glycuronic acid residues is named by replacing '-ic acid' by
'-an'. The generic name for this group of polysaccharides is 'glycuronan'.
Example:
O COOH O
L
"--J-;OH
(1-->4)-(z-o-galacturonan (pectin component)
Note. The term glycuronan is used instead of 'polyuronide'; the latter term is incorrect.
2-Carb-39.6. Amino sugar derivatives
A polysaccharide composed entirely of amino sugar residues is named by appropriate modification of the
systematic amino sugar name.
85
Example:
[4)-~-D-Glcp NAc(1 "-~]n
(1--~4)-2-acetamido-2-deoxy-13-D-glucan (chitin)
2-Carb-39.7. Polysaeeharides composed of more than one kind of residue
A heteropolysaccharide (heteroglycan) is a polymer containing two or more kinds of sugar (glycose) or
modified sugar (e.g. aminodeoxyglycose or glyeuronic acid) residue. When the polysaccharide has a principal
chain ('backbone') composed of only one type of sugar residue, this residue should be cited last (as a 'glycan'
term), and the other types of residue cited as 'glyco-' prefixes in alphabetical order. However, when no single
type of sugar residue constitutes the principal chain, all sugar residues should be cited alphabetically as
'glyco-' prefixes, and the name should terminate with the suffix '-glycan'.
Examples:
C¢-D-Galp
1
J.
6
[4)-13-D-Manp-(1-~4)-13-D-ganp-(1---~]n
A D-galacto-D-mannan (guaran)
Note. A less branched D-galacto-D-mannan could be shown in the short form as:
Galcc-6
Galct-6
I
I
[4Manl3-]n4Manl3-[4Man[~-]n4Man[3-.
[4)-I3-1)-Glcp-(1-~4)-t~-D-Glcp-(1 --~]n
3
T
1
13-o-Manp-(1 -~4)-~D-GlcpA-(1 --)2)-et-o-Manp6Ac
6 4
\/
CH3CCO2Xanthan
2-Carb-39.8. Substituted residues
When substitution occurs in a polysaccharide (glycan), each type of substitutent is cited in the name at an
appropriate position (in alphabetical order).
Examples:
H.
°.
0
H0 .~.,,,,~'~.~.~
H O ~ O M e
OH
(4-O-Methyl-¢-D-glucurono)-D-xylan
o.
86
L
--j-oo.
2,3-Di-O-acetyl-6-O-trib/lamylose
[4)-I3-D-GlcpA-(I~3)-~-D-GlcpNAc-(I~]n
(2-Acetamido-2-deoxy-D-gluco)-D-glucuronoglycan(hyaluronic acid or hyaluronan)
2-Carb-39.9. Glycoproteins, glycopeptides and peptidoglycans
Polymers containing covalently bound monosaccharide and amino-acid residues are termed glycoproteins,
glycopeptides or peptidoglycans. It is not possible to give precise distinctions between these terms. In general,
glycoproteins are conjugated proteins containing either oligosaccharide groups or polysaccharide groups
having a fairly low relative molecular mass. Proteoglycans are proteins linked to polysaccharides of high
molecular mass. Peptidoglycans consist of polysaccharide chains covalently linked to peptide chains. The
nomenclature of these compounds is discussed in [! 1].
Synthetically produced or modified carbohydrate-protein conjugates are sometimes referred to as neoglycoproteins. The nomenclature for the carbohydrate-containing substituents in such structures is analogous to
sequential oligosaccharide nomenclature (2-Carb-37.2)
Examples:
O--[CH218--CO--INH (of protein)
F
<I
CH2OMe
?
IHO~
°, H3C~'---01#
>"
|
L
oH
,
OMe
J
Poly-[(3,6-Di-O-methyl-~-D-glucopyranosyl)-(1-~4)-(2,3-di-O-methyl-~-L-rhamnopyranosyl)-(1--~2)-(3-O-methyl-ec-Lrhamnopyranosyloxy)-(1-O--,9)-nonanoyl-(l~N]-protein
{[I~-D-Glcp3,6Me2-(1--->4)-~-L-Rhap2,3Me2-(1-->2)-e~-L-Rhap3Me-(1-O-->9)-nonanoyl-(1-)N]n-protein}
protein)
H3C...~..~0 ~
~
J
FH
CH2OMe
IO
o-~----_k_J o H3C'#"---OJ)
/ M e O ' ~ ' ~ O'~'~'~
L
OH
OMe /Me
J
Poly-[(3,6-Di-O-methyl-lB-D-gtucopyranosyl)-(1--~4)-(2,3-di-O-methyl-c~-L-rhamnopyranosyl)-(1--~2)-(3-O-methyl-a-Lrhamnopyranosyloxy)-(1-O~4')-(3-phenylpropanoyl)-(1--)NLyS]-protein
87
References
1. IUPAC Commission on the Nomenclature of Organic Chemistry (CNOC) and IUPAC-IUB Commission on
Biochemical Nomenclature (CBN), Tentative rules for carbohydrate nomenclature, Part I, 1969, Biochem J., 125,
673-695 (1971); Biochemistry, 10, 3983-4004 (1971); Biochim. Biophys. Acta, 244, 223-302 (1971); Eur. J. Biochem.,
21, 455-477 (1971) and 25, 4 (1972); J. Biol. Chem., 247, 613-635 (1972);ref.2, pp.127-148.
2. International Union of Biochemistry and Molecular Biology, 'Biochemical Nomenclature and Related Documents',
Portland Press, London (1992).
3. IUPAC-IUB Joint Commission on Biochemical Nomenclature (JCBN), Conformational nomenclature for five- and
six-membered ring forms of monosaccharides and their derivatives (Recommendations 1980), Eur.J.Biochem. U l ,
295-298 (1980); Arch. Biochem. Biophys., 207, 469-472 (1981); Pure Appl. Chem., 53, 1901-1905 (1981); ref. 2, pp.
158-161.
4. 1UPAC-IUB Joint Commission on Biochemical Nomenclature (JCBN), Nomenclature of branched-chain monosaccharides (Recommendations 1980), Eur. J. Biochem,, 119, 5-8 (1981); corrections: Eur. J. Biochem., 125, 1 (1982);
Pure Appl. Chem., 54, 211-215 (1982); ref.2, pp. 165-168.
5. IUPAC-IUB Joint Commission on Biochemical Nomenclature (JCBN), Nomenclature of unsaturated monosaccharides (Recommendations 1980), Eur. J. Biochem., 119, 1-3 (1981); corrections: Eur. J. Biochem., 125, 1 (1982); Pure
Appl. Chem., 54, 207-210 (1982); ref.2, pp. 162-164.
6. IUPAC-IUB Joint Commission on Biochemical Nomenclature (JCBN), Abbreviated terminology of oligosaccharide
chains (Recommendations 1980), J. Biol. Chem., 257, 3347-3351 (1982); Eur. J. Biochem., 126, 433-437 (1982); Pure
Appl. Chem., 54, 1517-1522 (1982); Arch. Biochem. Biophys., 220, 325-329 (1983); ref. 2, pp. 169-173.
7. IUPAC-IUB Joint Commission on Biochemical Nomenclature (JCBN), Polysaccharide nomenclature (Recommendations 1980), Eur. J. Biochem., 126, 439-441 (1982); Pure Appl. Chem., 54, 1523-1526 (1982); J. Biol. Chem., 257,
3352-3354 (1982); Arch. Biochem. Biophys., 220, 330-332 (1983); ref. 2, pp. 174-176.
8. IUPAC-IUB Commission on Biochemical Nomenclature (CBN), Nomenclature of cyclitols (Recommendations
1973), Biochem. J., 153, 23-31 (1976); Eur. J. Biochem., 57, 1-7 (1975); Pure Appl. Chem., 37, 283-297 (1974); ref. 2,
pp. 149-155.
9. Nomenclature Committee of IUB (NC-IUB), Numbering of atoms in myo-inositol (Recommendations 1988),
Biochem. J., 258, 1-2 (1989); Eur. J. Biochem., 180, 485-486 (1989); ref.2, pp. 156-157.
10. IUPAC-IUB Joint Commission on Biochemical Nomenclature (JCBN), Symbols for specifying the conformation
of polysaccharide chains (Recommendations 1981), Eur. J. Biochem, 131, 5-7, (1983); PureAppl. Chem., 55, 1269-1272
(1983); ref. 2, pp. 177-179.
11. IUPAC-IUB Joint Commission on Biochemical Nomenclature (JCBN), Nomenclature of glycoproteins, glycopeptides and peptidoglycans, Eur. J. Biochem., 159, 1-6 (1986); Glycoconjugate J., 3, 123-124 (1986); J. Biol. Chem., 262,
13-18 (1987); Pure Appl. Chem., 60, 1389-1394 (1988); Royal Society of Chemistry Specialist Periodical Report,
'Amino Acids and Peptides', vol. 21, p. 329 (1990); ref. 2, pp. 84-89.
12. IUPAC-IUB Joint Commission on Biochemical Nomenclature (JCBN), Nomenclature of glycolipids, in preparation.
13. IUPAC Nomenclature of Organic Chemistry, Sections A, B, C, D, E, F and H, 1979 Edition, Pergamon Press,
Oxford, U.K. Sections E and F are reprinted in ref. 2, pp. 1-18 and 19-26, respectively.
14. Guide to IUPAC Nomenclature of Organic Compounds, Recommendations 1993, Blackwell Scientific Publications,
Oxford (1993).
15. This text is largely based on an essay entitled 'Development of Carbohydrate Nomenclature' by D. Horton, included
in 'The Terminology of Biotechnology: A Multidisciplinary Problem' (ed. K.L. Loening, Springer-Verlag, Berlin and
Heidelberg, 1990).
16. E. Fischer, Ber., 23, 2114 (1890).
17. Rules of carbohydrate nomenclature (1948), Chem. Eng. News, 26, 1623 (1948).
18. Rules of carbohydrate nomenclature (1952), J. Chem. Soc., 5108 (1952); Chem. Eng. News, 31, 1776 (1956).
19. Rules of carbohydrate nomenclature (1963), J. Org. Chem., 28, 281 (1963).
20. IUPAC Commission on Macromolecular Nomenclature, Nomenclature of regular single-strand organic polymers
(Recommendations 1975), Pure Appl. Chem., 48, 373-385 (1976); 'Compendium of Macromolecular Nomenclature',
Blackwell Scientific Publications, Oxford, p.91 (1991).
21. IUPAC-IUB Joint Commission on Biochemical Nomenclature (JCBN), The nomenclature of lipids (Recommendations 1976), Eur. J. Biochem., 79, 11-21 (1977); Hoppe-Seyler's Z. Physiol. Chem., 358, 617-631 (1977); Lipids, 12,
88
455-468 (1977); Mol. Cell, Biochem., 17, 157-171 (1977); Chem. Phys. Lipids, 21, 159-173 (1978); J. LipidRes., 19,
114-40728 (1978); Biochem. J., 171, 21-35 (1978); ref. 2, pp. 180-191.
22. D. Cremer and J.A. Pople, J. Am. Chem. Soc., 97, 1354-1358 (1975): J.C.A. Boeyens, J. Cryst. Mol. Struct., 8,
317-320 (1978); P. KSII, H.-G. John, and J. Kopf, Liebigs Ann. Chem., 626-638 (1982).
23. IUB Nomenclature Committee, 'Enzyme Nomenclature', Academic Press, Orlando, Florida (1992).
24. IUPAC-IUB Commission on Biochemical Nomenclature (CBN), Nomenclature of phosphorus-containing compounds of biochemical importance (Recommendations 1976), Hoppe-Seylers Z. Physiol. Chem., 358, 599-616 (1977);
Eur. J. Biochem., 79, 1-9 (1977); Proc. Natl. Acad. Sci. USA, 74, 2222-2230 (1977); Biochem. J., 171, 1-19 (1978); ref.
2. pp. 256-265.
25. IUPAC Commission on Nomenclature of Organic Chemistry, Revised nomenclature for radicals, ions, radical ions
and related species (Recommendations 1993), Pure Appl. Chem., 65, 1357-1455 (1993).
26. IUPAC Nomenclature of Organic Chemistry, Section F, revised version in preparation.
27. IUPAC Commission on Nomenclature of Organic Chemistry, Revision of the extended Hantzsch-Widman system
of nomenclature for heteromonocycles, Pure Appl. Chem., 55, 409-416 (1983).
89
APPENDIX
Trivial Names for Carbohydrates and Derivatives
with their Systematic Equivalents and Symbols
(non-limiting list)
(a) parent monosaccharides
AIIose (All)
Altrose (AIt)
Arabinose (Am)
Erythrose
Erythrulose
Fructose (Fru)
D-Fucitol (D-Fuc-oI)
L-FucitoI (L-Fuc-ol)
Fucosamine (FucN)
Fucose (Fuc)
Galactosamine (GAIN)
D-Galactosaminitol (GalN-ol)
Galactose (Gal)
Glucosamine (GIcN)
Glucosaminitol (GIcN-ol)
Glucose (GIc)
Glyceraldehyde
Glycerol (Gro)
Glycerone
(1,3-dihydroxyacetone)
Gulose (Gul)
Idose (Ido)
Lyxose (Lyx)
Mannosamine (ManN)
Mannose (Man)
Psicose (Psi)
Quinovose (Qui)
Quinovosamine
Rhamnitol (Rha-ol)
Rhamnosamine (RhaN)
Rhamnose (Rha)
Ribose (Rib)
Ribulose (Rul)
Sorbose (Sor)
Tagatose (Tag)
Talose (Tal)
Tartaric acid
Threose
Xylose (Xyl)
Xylulose (Xul)
allo-Hexose
altro-Hexose
arabino-Pentose
erythro-Tetrose
glycero-Tetrulose
arabino-Hex-2-ulose
6-Deoxy-o-galactitol
1-Deoxy-D-galactitol
2-Amino-2,6-dideoxygalactose
6-Deoxygalactose
2-Amino-2-deoxygalactose
2-Amino-2-deoxy-D-gatactitol
galacto-Hexose
2-Amino-2-deoxyglucose
2-Amino-2-deoxyglucitol
gluco-Hexose
2,3-Dihyd roxypropanal
Propane-1,2,3-triol
1,3-Dihyd roxypropanone
gulo-Hexose
ido-Hexose
lyxo-Pentose
2-Amino-2-deoxymannose
manno-Hexose
ribo-Hex-2-ulose
6-Deoxyglucose
2-Amino-2,6-dideoxyglucose
1-Deoxymannitol
2-Amino-2,6-dideoxymannose
6-Deoxymannose
r/bo-Pentose
erythro-Pent-2-ulose
xylo-Hexo2-ulose
lyxo-Hex-2-ulose
talo-Hexose
Erythraric/Threaric acid
threo-Tetrose
xylo-Pentose
threo-Pent-2-ulose
90
(b) c o m m o n trivial n a m e s
Abequose (Abe)
Amicetose
Amylose
Apiose (Api)
Arcanose
Ascarylose
Ascorbic acid
Boivinose
Cellobiose
Cellotriose
Chacotriose
Chalcose
Cladinose
Colitose
Cymarose
2-Deoxyribose (dRib)
2-Deoxyglucose (2dGIc)
Diginose
Digitalose
Digitoxose
Evalose
Evernitrose
Gentianose
Gentiobiose
Hamamelose
Inulin
Isolevoglucosenone
Isomaltose
Isomaltotriose
Isopanose
Kojibiose
Lactose (Lac)
Lactosamine (LacN)
Lactosediamine (LacdiN)
Laminarabiose
Levoglucosan
Levoglucosenone
Maltose
Manninotriose
Melezitose
Melibiose
Muramic acid (Mur)
Mycarose
Mycinose
3,6-Dideoxy-D-xylo-hexose
2,3,6-Trideoxy-D-erythro-hexose
(1--)4)-c(-g-Glucopyranan
3-C-(Hydroxymethyl)-glycero-tetrose
2,6-Dideoxy-3-C-methyl-3-O-methyl-xylo-hexose
3,6-Dideoxy-L-arabino-hexose
L-threo-Hex-2-enono-1,4-1actone
2,6-Dideoxy-D-gulose
~-D-Glucopyranosyl-(1-->4)-D-glucose
13-D-Glucopyranosyl-(1--)4)-J3-g-glucopyranosyl-(1--)4)-D-glucose
C(-L-Rhamnopyranosyl-(1--)2)-[c(-L-rhamnopyranosyl-(1-~4)]-D-glucose
4,6-Dideoxy-3-O-methyl-D-xylo-hexose
2,6-Dideoxy-3-C-methyl-3-O-methyl-L-r/bo-hexose
3,6- Dideoxy-L-xy/o-hexose
6-Deoxy-3-O-methyl-r/bo-hexose
2-Deoxy-erythro-pentose
2-Deoxy-arabino-hexose
2,6-Dideoxy-3- O-methyl-lyxo-hexose
6-Deoxy-3-O-methyI-D-galactose
2,6-Dideoxy-D-r/bo-hexose
6-Deoxy-3- C-methyI-D-mannose
2,3,6-Trideoxy-3-C-methyl-4-O-rnethyl-3-nitro-L-arabino-hexose
13-D-Fructofuranosyl ~-D-glucopyranosyl-(1--)6)-c~-D-glucopyranoside
13-D-Glucopyranosyl-(1--)6)-D-glucose
2-C-(Hydroxymethyl)-D-ribose
(2--~l)-13-D-Fructofuranan
1,6-Anhydro-2,3-dideoxy-~-o-glycero-hex-2-enopyranos-4-ulose
C(-D-Glucopyranosyl-(1--)6)-I:)-glucose
~-D-Glucopyranosyl-(1 --)6)-C(-D-glucopyranosyl-(1--)6)-D-glucose
c~-D-Glucopyranosyl-(1--->4)-[cc-o-glucopyranosyl-(1---)6)]-D-glucose
(x-D-Glucopyranosyl-(1--)2)-D-glucose
~-D-Galactopyranosyl-(1--)4)-D-glucose
13-D-Galactopyranosyl-(1--)4)-D-glucosamine
2-Amino-2-deoxy-~-D-galactopyranosyl-(1-->4)-D-glucosamine
13-D-Glucopyranosyl-(1--)3)-D-glucose
1,6-Anhydro-13-D-glucopyranose
1,6-Anhydro-3,4-dideoxy-[3-D-glycero-hex-3-enopyranos-2-ulose
c(-D-Glucopyranosyl-(1 --)4)-D-glucose
C(-D-Galactopyranosyl-(1-~6)-c(-o-galactopyranosyl-(1 ~6)-D-glucose
c(-D-Glucopyranosyl-(1 --)3)-~-D-fructofuranosyl oC-D-glucopyranoside
C~-D-Galactopyranosyl-(1~6)-D-glucose
2-Amino-3-O-[(R)-I -carboxyethyl]-2-deoxy-l::)-glucose
2,6-Dideoxy-3-C-rnethyI-L-ribo-hexose
6-Deoxy-2,3-di- O-methyI-D-allose
91
Neuraminic acid (Neu)
Nigerose
Nojirimycin
Noviose
Oleandrose
Panose
Paratose
Planteose
Primeverose
Raffinose
Rhodinose
Rutinose
Sarmentose
Sedoheptulose
Sedoheptulosan
Solatriose
Sophorose
Stachyose
Streptose
Sucrose
(saccharose)
c(,oc-Trehalose
Trehalosamine
Turanose
Tyvelose (Tyv)
Umbelliferose
5-Amino-3,5-dideoxy-o-glycero-D-galacto-non-2-ulosonic acid
C(-D-Glucopyranosyl-(1--)3)-D-glucose
5-Amino-5-deoxy-D-glucopyranose
6-Deoxy-5-C-methyl-4-O-methyI-L-lyxo-hexose
2,6-Dideoxy-3-O-methyI-L-arabino-hexose
(z-D-Glucopyranosyl-(1~6)-C~-D-glucopyranosyl-(1-->4)-D-glucose
3,6-Dideoxy-D-ribo-hexose
¢-D-Galactopyranosyl-(l-->6)-13-D-fructofuranosyl (z-o-glucopyranoside
~-D-Xylopyranosyl-(1~6)-o-glucose
I~-D-Fructofuranosyl (~-D-galactopyranosyl-(1--)6)-(z-D-glucopyranoside
2,3,6-Trideoxy-L-threo-hexose
c(-L-Rhamnopyranosyl-(1--)6)-D-glucose
2,6-Dideoxy-3-O-methyI-D-xylo-hexose
D-altro-Hept-2-ulose
2,7-Anhydro-~-D-altro-hept-2-ulopyranose
c(-L-Rhamnopyranosyl-(1--)2)-[13-D-glucopyranosyl-(1--)3)]-D-galactose
13-D-Glucopyranosyl-(1--)2)-D-glucose
J~-D-Fructofuranosyl (Z-D-galactopyranosyl-(1--->6)-c(-D-galactopyranosyl-(1--)6)-(~-Dglucopyranoside
5-Deoxy-3- C-formyl-L-lyxose
13-D-Fructofuranosyl e{-D-glucopyranoside
c~-D-Glucopyranosyl (Z-D-glucopyranoside
2-Amino-2-deoxy-(~-D-glucopyranosyl CC-D-glucopyranoside
(~-D-Glucopyranosyl-(1---)3)-o-fructose
3,6-Dideoxy.D-arabino-hexose
13-D-Fructofuranosyl ~-D-galactopyranosyl-(l~2)-(~-D-galactopymnoside
(c) trivial names formed by modification of non-standard monosaccharide parent names
Acosamine
Bacillosamine
Oaunosamine
Desosamine
Forosamine
Garosamine
Kanosamine
Kansosamine
Mycaminose
Mycosamine
Perosamine
Pneumosamine
Purpurosamine C
Rhodosamine
3-Amino-2,3,6-t rideoxy-L-xylo-hexose
2,4-Diamino-2,4,6-tddeoxy-o-glucose
3-Amino-2,3,6-trideoxy-L-lyxo-hexose
3,4,6-Trideoxy-3-dimethylamino-o-xylo-hexose
2,3,4,6-Tetradeoxy-4-dimethylamino-D-erythro-hexose
3-Deoxy-4- C-methyl-3-methylamino-L-arabinose
3-Amino-3-deoxy-D-glucose
4,6-Dideoxy-3- C-methyl-2- O-methyI-L-mannose
3,6-Dideoxy-3-dimethytamino-D-glucose
3-Amino-3,6-dideoxy-D-mannose
4-Amino-4,6-dideoxy-D-mannose
2-Amino-2,6-dideoxy-D-talose
2,6-Diamino-2,3, 4,6-tetradeoxy-D-erythro-hexose
2,3,6-Trideoxy-3-dimethylamino- lyxo-hexose
92
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